methyl 2-oxo-2-(1H-pyrrol-2-yl)acetate

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A suspension of 10 g (65 mmol) of methyl pyrrol-2-ylglyoxylate in 100 ml of ether is added to a solution of 1.7 g (6.5 mmol) of 18-crown-6 with 7.3 g (65 mmol) of potassium tert-butylate in 100 ml of ether, stirring is carried out for 30 minutes and 11.1 g (65 mmol) of benzyl bromide in 50 ml of ether are then added dropwise. Stirring is carried out overnight at room temperature, the mixture is poured onto water and extracted with ether and the organic phase is dried and evaporated down. Chromatography over silica gel with hexane/ethyl acetate gives 6.7 g (42%) of the title compound as a reddish brown oi. Stirring is carried out overnight at room temperature the mixture is poured onto water extracted with ether the organic phase is dried evaporated down

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 97.5 g (1.2 eq) of methoxyamine hydrochloride are added to a solution of 148.8 g (0.97 mol) of methyl pyrrol-2-ylglyoxylate (prepared by a method similar to that described by B. Lindstrom et al., Acta Chem. Scand. 27 (1973), 7) in 1 l of methanol, and the solution is refluxed for 2.5 hours. After evaporation in a rotary evaporator, the residue is taken up in ethyl acetate and the solution is washed with water, dried and evaporated down. 81 g (46%) of the pyrrole remained in the form of an oil. prepared by a method similar to After evaporation in a rotary evaporator the solution is washed with water dried evaporated down

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Methyl pyrrol-2-ylglyoxylate (306 mg) in diglyme was treated with sodium hydride (63 mg) and stirred at room temperature for 3 hr. Benzyloxymethyl chloride (376 mg) was added and the mixture stirred at room temperature for a further 3 hr. The suspension was filtered and the filtrate evaporated. The residue, in ether, was washed with sodium bicarbonate solution, water and dried. Evaporation gave the crude product as a brown oil (530 mg). Purification by preparative thin-layer chromatography gave the title compound as a colourless oil (250 mg, 46%); τ values (DMSO-d6) include 6.10 (--CH3), 4.20 (>N-CH2 -), 5.47 (--OCH2 --), 2.70 (-Ph). the mixture stirred at room temperature for a further 3 hr The suspension was filtered the filtrate evaporated The residue, in ether, was washed with sodium bicarbonate solution, water dried Evaporation gave the crude product as a brown oil (530 mg) Purification by preparative thin-layer chromatography

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Methyl pyrrol-2-ylglyoxylate (306 mg) in diglyme was treated with sodium hydride (63 mg) and stirred at room temperature for 3 hr. Benzyloxymethyl chloride (376 mg) was added and the mixture stirred at room temperature for a further 3 hr. The suspension was filtered and the filtrate evaporated. The residue, in ether, was washed with sodium bicarbonate solution, water and dried. Evaporation gave the crude product as a brown oil (530 mg). Purification by preparative thin-layer chromatography gave the title compound as a colourless oil (250 mg, 46%); τ values (DMSO-d6) include 6.10 (--CH3), 4.20 (>N--CH2 --), 5.47 (--OCH2 --), 2.70 (--Ph). the mixture stirred at room temperature for a further 3 hr The suspension was filtered the filtrate evaporated The residue, in ether, was washed with sodium bicarbonate solution, water dried Evaporation gave the crude product as a brown oil (530 mg) Purification by preparative thin-layer chromatography

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Methyl pyrrol-2-ylglyoxylate (306 mg) in diglyme was treated with sodium hydride (63mg) and stirred at room temperature for 3 hr. Benzyloxymethyl chloride (376mg) was added and the mixture stirred at room temperature for a further 3 hr. The suspension was filtered and the filtrate evaporated. The residue, in ether, was washed with sodium bicarbonate solution, water and dried. Evaporation gave the crude product as a brown oil (530mg). Purification by preparative thin-layer chromatography gave the title compound as a colourless oil (250 mg,46%); τ values (DMSO-d6) include 6.10 (--CH3), 4.20 (N-CH2 --). 5.47 (--OCH2 --), 2.70 (--Ph). the mixture stirred at room temperature for a further 3 hr The suspension was filtered the filtrate evaporated The residue, in ether, was washed with sodium bicarbonate solution, water dried Evaporation gave the crude product as a brown oil (530mg) Purification by preparative thin-layer chromatography

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Methyl pyrrol-2-ylglyoxylate (306 mg) in diglyme was treated with sodium hydride (63 mg) and stirred at room temperature for 3 hr. Benzyloxymethyl chloride (376 mg) was added and the mixture stirred at room temperature for a further 3 hr. The suspension was filtered and the filtrate evaporated. The residue, in ether, was washed with sodium bicarbonate solution, water and dried. Evaporation gave the crude product as a brown oil (530 mg). Purification by preparative thin-layer chromatography gave the title compound as a colourless oil (250 mg, 46%); τ values (DMSO-d6) include 6.10 (--CH3), 4.20 (>N--CH2 --), 5.47 (--OCH2 --), 2.70 (--Ph). the mixture stirred at room temperature for a further 3 hr The suspension was filtered the filtrate evaporated The residue, in ether, was washed with sodium bicarbonate solution, water dried Evaporation gave the crude product as a brown oil (530 mg) Purification by preparative thin-layer chromatography

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Methyl pyrrol-2-ylglyoxylate (306 mg) in diglyme was treated with sodium hydride (63 mg) and stirred at room temperature for 3 hr. Benzyloxymethyl chloride (376 mg) was added and the mixture stirred at room temperature for a further 3 hr. The suspension was filtered and the filtrate evaporated. The residue, in ether, was washed with sodium bicarbonate solution, water and dried. Evaporation gave the crude product as a brown oil (530 mg). Purification by preparative thin-layer chromatography gave the title compound as a colourless oil (250 mg, 46%); τ values (DMSO-d6) include 6.10 (--CH3), 4.20 (>N--CH2 --), 5.47 (--OCH2 --), 2.70 (--Ph). the mixture stirred at room temperature for a further 3 hr The suspension was filtered the filtrate evaporated The residue, in ether, was washed with sodium bicarbonate solution, water dried Evaporation gave the crude product as a brown oil (530 mg) Purification by preparative thin-layer chromatography

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Methyl pyrrol-2-ylglyoxylate (306 mg) in diglyme was treated with sodium hydride (63mg) and stirred at room temperature for 3 hr. Benzyloxymethyl chloride (376mg) was added and the mixture stirred at room temperature for a further 3 hr. The suspension was filtered and the filtrate evaporated. The residue, in ether, was washed with sodium bicarbonate solution, water and dried. Evaporation gave the crude product as a brown oil (530mg). Purification by preparative thin-layer chromatography gave the title compound as a colourless oil (250 mg,46%); τ values (DMSO-d6) include 6.10 (--CH3), 4.20 (>N-CH2 --), 5.47 (--OCH2 --), 2.70 (--Ph). the mixture stirred at room temperature for a further 3 hr The suspension was filtered the filtrate evaporated The residue, in ether, was washed with sodium bicarbonate solution, water dried Evaporation gave the crude product as a brown oil (530mg) Purification by preparative thin-layer chromatography

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Methyl pyrrol-2-ylglyoxylate (306 mg) in diglyme was treated with sodium hydride (63mg) and stirred at room temperature for 3 hr. Benzyloxymethyl chloride (376mg) was added and the mixture stirred at room temperature for a further 3 hr. The suspension was filtered and the filtrate evaporated. The residue, in ether, was washed with sodium bicarbonate solution, water and dried. Evaporation gave the crude product as a brown oil (530mg.). Purification by preparative thin-layer chromatography gave the title compound as a colourless oil (250 mg, 46%); τ values (DMSO-d6) include 6.10 (--CH3), 4.20 (>N--CH2 --), 5.47 (--OCH2 --), 2.70 (-Ph). the mixture stirred at room temperature for a further 3 hr The suspension was filtered the filtrate evaporated The residue, in ether, was washed with sodium bicarbonate solution, water dried Evaporation gave the crude product as a brown oil (530mg.) Purification by preparative thin-layer chromatography

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Methyl pyrrol-2-ylglyoxylate (306 mg) in diglyme was treated with sodium hydride (63mg) and stirred at room temperature for 3 hr. Benzyloxymethyl chloride (376mg) was added and the mixture stirred at room temperature for a further 3 hr. The suspension was filtered and the filtrate evaporated. The residue, in ether, was washed with sodium bicarbonate solution, water and dried. Evaporation gave the crude product as a brown oil (530mg.). Purification by preparative thin-layer chromatography gave the title compound as a colourless oil (250 mg, 46%); τ values (DMSO-d6) include 6.10 (--CH3), 4.20 (>N--CH2 --), 5.47 (--OCH2 --), 2.70 (-Ph). the mixture stirred at room temperature for a further 3 hr The suspension was filtered the filtrate evaporated The residue, in ether, was washed with sodium bicarbonate solution, water dried Evaporation gave the crude product as a brown oil (530mg.) Purification by preparative thin-layer chromatography

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Methyl pyrrol-2-ylglyoxylate (306 mg) in diglyme was treated with sodium hydride (63mg) and stirred at room temperature for 3 hr. Benzyloxymethyl chloride (376mg) was added and the mixture stirred at room temperature for a further 3 hr. The suspension was filtered and the filtrate evaporated. The residue, in ether, was washed with sodium bicarbonate solution, water and dried. Evaporation gave the crude product as a brown oil (530mg). Purification by preparative thin-layer chromatography gave the title compound as a colourless oil (250 mg,46%); τ values (DMSO-d6) include 6.10 (--CH3), 4.20 (>N--CH2 --), 5.47 (--OCH2 --), 2.70 (--Ph). the mixture stirred at room temperature for a further 3 hr The suspension was filtered the filtrate evaporated The residue, in ether, was washed with sodium bicarbonate solution, water dried Evaporation gave the crude product as a brown oil (530mg) Purification by preparative thin-layer chromatography

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A suspension of 10 g (65 mmol) of methyl pyrrol-2-ylglyoxylate in 100 ml of ether is added to a solution of 1.7 g (6.5 mmol) of 18-crown-6 with 7.3 g (65 mmol) of potassium tert-butylate in 100 ml of ether, stirring is carried out for 30 minutes and 11.1 g (65 mmol) of benzyl bromide in 50 ml of ether are then added dropwise. Stirring is carried out overnight at room temperature, the mixture is poured onto water and extracted with ether and the organic phase is dried and evaporated down. Chromatography over silica gel with hexane/ethyl acetate gives 6.7 g (42%) of the title compound as a reddish brown oi. Stirring is carried out overnight at room temperature the mixture is poured onto water extracted with ether the organic phase is dried evaporated down