3-(3-hydroxyphenyl)propanenitrile

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

実験手順: A solution of 3-(3-hydroxyphenyl)propanenitrile (Step B, 1.25 g, 8.5 mmol) and diisopropyl azodicarboxylate (DIAD, 1.87 g, 9.26 mmol) in dry THF (10 ml) was added drop wise to a solution of 2,6-Dimethylbenzyl alcohol (1.27 g, 9.3 mmol) and triphenylphosphine (TPP, 2.43 g, 9.26 mmol) in dry THF (30 ml) at 0° C. under argon. The reaction mixture was warmed to room temperature for 4 hours or until all the starting material is consumed, diluted with ether and washed with water (2×). The organic layer was dried over Na2SO4, filtered, concentrated, and purified by flash chromatography on a silica gel column (hex: ethyl acetate 2:1) to give the title compound. is consumed diluted with ether washed with water (2×) The organic layer was dried over Na2SO4 filtered concentrated purified by flash chromatography on a silica gel column (hex: ethyl acetate 2:1)

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

実験手順: To a stirred solution of 3-(3-methoxyphenyl)propanenitrile (Step A, 1.71 g, 10.6 mmol) in dry CH2Cl2 (20 ml) was added BBr3 (1M in CH2Cl2, 5.32 g, 21.2 mmol) at −78° C. under argon. The reaction mixture was stirred at the same temperature for 2 hours and then at 0° C. for 4 hours or until all the starting material is consumed, quenched with ice, extracted with EtOAc (30 ml×3), the combined organic layer was washed carefully with sat NaHCO3, brine and dried over Na2SO4, filtered, concentrated, and purified by flash chromatography on a silica gel column (hex: ethyl acetate 2:1) to give the title compound. at 0° C. for 4 hours until all the starting material is consumed quenched with ice extracted with EtOAc (30 ml×3) the combined organic layer was washed carefully with sat NaHCO3, brine dried over Na2SO4 filtered concentrated purified by flash chromatography on a silica gel column (hex: ethyl acetate 2:1)

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

実験手順: A solution of 3-(3-hydroxyphenyl)propanenitrile (Step B, 1.25 g, 8.5 mmol) and diisopropyl azodicarboxylate (DIAD, 1.87 g, 9.26 mmol) in dry THF (10 ml) was added drop wise to a solution of 2,6-Dimethylbenzyl alcohol (1.27 g, 9.3 mmol) and triphenylphosphine (TPP, 2.43 g, 9.26 mmol) in dry THF (30 ml) at 0° C. under argon. The reaction mixture was warmed to room temperature for 4 hours or until all the starting material is consumed, diluted with ether and washed with water (2×). The organic layer was dried over Na2SO4, filtered, concentrated, and purified by flash chromatography on a silica gel column (hex: ethyl acetate 2:1) to give the title compound. is consumed diluted with ether washed with water (2×) The organic layer was dried over Na2SO4 filtered concentrated purified by flash chromatography on a silica gel column (hex: ethyl acetate 2:1)

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

実験手順: To a stirred solution of 3-(3-methoxyphenyl)propanenitrile (Step A, 1.71 g, 10.6 mmol) in dry CH2Cl2 (20 ml) was added BBr3 (1M in CH2Cl2, 5.32 g, 21.2 mmol) at −78° C. under argon. The reaction mixture was stirred at the same temperature for 2 hours and then at 0° C. for 4 hours or until all the starting material is consumed, quenched with ice, extracted with EtOAc (30 ml×3), the combined organic layer was washed carefully with sat NaHCO3, brine and dried over Na2SO4, filtered, concentrated, and purified by flash chromatography on a silica gel column (hex: ethyl acetate 2:1) to give the title compound. at 0° C. for 4 hours until all the starting material is consumed quenched with ice extracted with EtOAc (30 ml×3) the combined organic layer was washed carefully with sat NaHCO3, brine dried over Na2SO4 filtered concentrated purified by flash chromatography on a silica gel column (hex: ethyl acetate 2:1)

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

実験手順: To a stirred solution of 3-(3-methoxyphenyl)propanenitrile (Step A, 1.71 g, 10.6 mmol) in dry CH2Cl2 (20 ml) was added BBr3 (1M in CH2Cl2, 5.32 g, 21.2 mmol) at −78° C. under argon. The reaction mixture was stirred at the same temperature for 2 hours and then at 0° C. for 4 hours or until all the starting material is consumed, quenched with ice, extracted with EtOAc (30 ml×3), the combined organic layer was washed carefully with sat NaHCO3, brine and dried over Na2SO4, filtered, concentrated, and purified by flash chromatography on a silica gel column (hex: ethyl acetate 2:1) to give the title compound. at 0° C. for 4 hours until all the starting material is consumed quenched with ice extracted with EtOAc (30 ml×3) the combined organic layer was washed carefully with sat NaHCO3, brine dried over Na2SO4 filtered concentrated purified by flash chromatography on a silica gel column (hex: ethyl acetate 2:1)

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

実験手順: A solution of 3-(3-hydroxyphenyl)propanenitrile (Step B, 1.25 g, 8.5 mmol) and diisopropyl azodicarboxylate (DIAD, 1.87 g, 9.26 mmol) in dry THF (10 ml) was added drop wise to a solution of 2,6-Dimethylbenzyl alcohol (1.27 g, 9.3 mmol) and triphenylphosphine (TPP, 2.43 g, 9.26 mmol) in dry THF (30 ml) at 0° C. under argon. The reaction mixture was warmed to room temperature for 4 hours or until all the starting material is consumed diluted with ether and washed with water (2×). The organic layer was dried over Na2SO4, filtered, concentrated, and purified by flash chromatography on a silica gel column (hex:ethyl acetate 2:1) to give the title compound. is consumed diluted with ether washed with water (2×) The organic layer was dried over Na2SO4 filtered concentrated purified by flash chromatography on a silica gel column (hex:ethyl acetate 2:1)

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

実験手順: To a stirred solution of 3-(3-methoxyphenyl)propanenitrile (Step A, 1.71 g, 10.6 mmol) in dry CH2Cl2 (20 ml) was added BBr3 (1M in CH2Cl2, 5.32 g, 21.2 mmol) at −78° C. under argon. The reaction mixture was stirred at the same temperature for 2 hours and then at 0° C. for 4 hours or until all the starting material is consumed, quenched with ice, extracted with EtOAc (30 ml×3), the combined organic layer was washed carefully with sat NaHCO3, brine and dried over Na7SO4, filtered, concentrated, and purified by flash chromatography on a silica gel column (hex:ethyl acetate 2:1) to give the title compound. at 0° C. for 4 hours until all the starting material is consumed quenched with ice extracted with EtOAc (30 ml×3) the combined organic layer was washed carefully with sat NaHCO3, brine dried over Na7SO4 filtered concentrated purified by flash chromatography on a silica gel column (hex:ethyl acetate 2:1)

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

実験手順: A 300 ml. flask equipped with a magnetic stirrer, cold water condenser, CO2 outlet and bubbler, and a heated oil bath was charged with 21 g. of crude α-cyano-m-hydroxydihydrocinnamic acid (above) and freshly redistilled quinoline (10 ml.). The acid underwent smooth decarboxylation at an oil bath temperature of 150°C with CO2 evolution ceasing after about 2.5 hr. For workup, the cooled mixture was treated with 200 ml. of 5N HCl and extracted thoroughly with several portions of diethyl ether totalling 350 ml. The ether was washed with water (1 × 100 ml.), saturated NaHCO3 (4 × 50 ml.), brine (1 × 100 ml.), and dried over anhydrous Na2SO4. Concentration of the ether solution gave 11.15 g. (69% yield) of β-(m-hydroxyphenyl)propionitrile as a pale yellow solid. Recrystallization from ethyl acetate/hexane gave the pure compound as light yellow crystals, m.p. 64°-66°C. flask equipped with a magnetic stirrer, cold water condenser, CO2 outlet bubbler, and a heated oil bath was charged with 21 g temperature of 150°C For workup, the cooled mixture was treated with 200 ml of 5N HCl and extracted thoroughly with several portions of diethyl ether totalling 350 ml The ether was washed with water (1 × 100 ml.), saturated NaHCO3 (4 × 50 ml.), brine (1 × 100 ml.) dried over anhydrous Na2SO4 Concentration of the ether solution gave 11.15 g

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

実験手順: A solution of 3-(3-hydroxyphenyl)propanenitrile (Step B, 1.25 g, 8.5 mmol) and diisopropyl azodicarboxylate (DIAD, 1.87 g, 9.26 mmol) in dry THF (10 ml) was added drop wise to a solution of 2,6-Dimethylbenzyl alcohol (1.27 g, 9.3 mmol) and triphenylphosphine (TPP, 2.43 g, 9.26 mmol) in dry THF (30 ml) at 0° C. under argon. The reaction mixture was warmed to room temperature for 4 hours or until all the starting material is consumed, diluted with ether and washed with water (2×). The organic layer was dried over Na2SO4, filtered, concentrated, and purified by flash chromatography on a silica gel column (hex: ethyl acetate 2:1) to give the title compound. is consumed diluted with ether washed with water (2×) The organic layer was dried over Na2SO4 filtered concentrated purified by flash chromatography on a silica gel column (hex: ethyl acetate 2:1)

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

実験手順: To a stirred solution of 3-(3-methoxyphenyl)propanenitrile (Step A, 1.71 g, 10.6 mmol) in dry CH2Cl2 (20 ml) was added BBr3 (1M in CH2Cl2, 5.32 g, 21.2 mmol) at −78° C. under argon. The reaction mixture was stirred at the same temperature for 2 hours and then at 0° C. for 4 hours or until all the starting material is consumed, quenched with ice, extracted with EtOAc (30 ml×3), the combined organic layer was washed carefully with sat NaHCO3, brine and dried over Na2SO4, filtered, concentrated, and purified by flash chromatography on a silica gel column (hex: ethyl acetate 2:1) to give the title compound. at 0° C. for 4 hours until all the starting material is consumed quenched with ice extracted with EtOAc (30 ml×3) the combined organic layer was washed carefully with sat NaHCO3, brine dried over Na2SO4 filtered concentrated purified by flash chromatography on a silica gel column (hex: ethyl acetate 2:1)