methyl 4-(3-oxoprop-1-enyl)benzoate

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: A solution of 0.21 g (1.25 mmoles) of 4-carbomethoxybenzaldehyde, 0.42 g (1.25 mmoles) of formylmethylenetriphenylphosphorane and a catalytic amount of benzoic acid in 25 ml of THF was refluxed under nitrogen for 18 hours. The THF was evaporated and the recovered gum extracted repeatedly with ether. The combined ether extracts were evaporated. Flash chromatography on silica gel with 50% CH2Cl2 /hexane up to 100% CH2Cl2 gave 90 mg of a white solid. The THF was evaporated the recovered gum extracted repeatedly with ether The combined ether extracts were evaporated

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

実験手順: A solution of 27.3 g (0.09 mole) of formyl methyltriphenyl phosphonium bromide and 14.8 g (0.09 mole) of p-carbomethoxybenzaldehyde in 900 ml of dry toluene was refluxed under nitrogen for 24 hr. After evaporating toluene under reduced pressure, the residue was chromatographed over silica column with 5% ethyl acetate in petroleum ether as eluant. The second fraction obtained by using 10% ethyl acetate in petroleum ether gave 4-carbomethoxycinnamaldehyde. Recrystallization from benzene gave 12.5 g 4-carbomethoxycinnamaldehyde, yield 73% m.p. 99°-101° C. The infrared spectrum showed absorption at 1720 cm-1 ##STR8## 1680 cm-1 (CHO), and 1620 cm-1 (--CH=CH--). NMR (CDCl3) showed δ3.8 (s, --COOCH3, 3) 6.5-7.1 (m,=CH--CHO, l), 7.3-7.6 (m, aromatic, 4), 7.9-8.1 (d, --CH=, l), and 9.8 (d, --CHO, l). Analysis calculated for C11H10O3 : C, 69.42%, H, 5.2%. Found: C, 68.69%, H, 5.25%. After evaporating toluene under reduced pressure the residue was chromatographed over silica column with 5% ethyl acetate in petroleum ether as eluant The second fraction obtained

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

実験手順: A solution of 27.3 g (0.09 mole) of formyl methyltriphenyl phosphonium bromide and 14.8 g (0.09 mole) of p-carbomethoxybenzaldehyde in 900 ml of dry toluene was refluxed under nitrogen for 24 hr. After evaporating toluene under reduced pressure, the residue was chromatographed over silica column with 5% ethyl acetate in petroleum ether as eluant. The second fraction obtained by using 10% ethyl acetate in petroleum ether gave 4-carbomethoxycinnamaldehyde. Recrystallization from benzene gave 12.5 g 4-carbomethoxycinnamaldehyde, yield 73% m.p. 99°-101° C. The infrared spectrum showed absorption at 1720 cm-1 ##STR8## 1680 cm-1 (CHO), and 1620 cm-1 (--CH=CH--). NMR (CDCl3) showed δ3.8 (s, --COOCH3, 3) 6.5-7.1 (m,=CH--CHO, l), 7.3-7.6 (m, aromatic, 4), 7.9-8.1 (d, --CH=, l), and 9.8 (d, --CHO, l). Analysis calculated for C11H10O3 : C, 69.42%, H, 5.2%. Found: C, 68.69%, H, 5.25%. After evaporating toluene under reduced pressure the residue was chromatographed over silica column with 5% ethyl acetate in petroleum ether as eluant The second fraction obtained

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: A solution of 27.3 g (0.09 mole) of formyl methyltriphenyl phosphonium bromide and 14.8 g (0.09 mole) of p-carbomethoxybenzaldehyde in 900 ml of dry toluene was refluxed under nitrogen for 24 hours. After evaporating toluene under reduced pressure, the residue was chromatographed over silica column with 5% ethyl acetate in petroleum ether as eluant. The second fraction obtained by using 10% ethyl acetate in petroleum ether gave 4-carbomethoxycinnamaldehyde. Recrystallization from benzene gave 12.5 g 4-carbomethoxycinnamaldehyde, yield 73% m.p. 99°-101° C. The infrared spectrum showed absorption at 1720 cm1 (COOCH3), 1680 cm-1 (CHO), and 1620 cm-1 (--CH=CH--). NMR (CDCl3) showed δ3.8 (s, --COOCH3, 3) 6.5-7.1 (m,=CH--CHO, 1), 7.3-7.6 (m, aromatic, 4), 7.9-8.1 (d, --CH=, 1), and 9.8 (d, --CHO, 1 ). Analysis calculated for C11H10O3 :C, 69.42%, H, 5.2%. Found: C, 68.69%, H, 5.26%. After evaporating toluene under reduced pressure the residue was chromatographed over silica column with 5% ethyl acetate in petroleum ether as eluant The second fraction obtained

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

実験手順: A solution of 0.21 g (1.25 mmoles) of 4-carbomethoxybenzaldehyde, 0.42 g (1.25 mmoles) of formylmethylenetriphenylphosphorane and a catalytic amount of benzoic acid in 25 ml of THF was refluxed under nitrogen for 18 hours. The THF was evaporated and the recovered gum extracted repeatedly with ether. The combined ether extracts were evaporated. Flash chromatography on silica gel with 50% CH2Cl2 /hexane up to 100% CH2Cl2 gave 90 mg of a white solid. The THF was evaporated the recovered gum extracted repeatedly with ether The combined ether extracts were evaporated

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

実験手順: A solution of 27.3 g (0.09 mole) of formyl methyltriphenyl phosphonium bromide and 14.8 g (0.09 mole) of p-carbomethoxybenzaldehyde in 900 ml of dry toluene was refluxed under nitrogen for 24 hr. After evaporating toluene under reduced pressure, the residue was chromatographed over silica column with 5% ethyl acetate in petroleum ether as eluant. The second fraction obtained by using 10% ethyl acetate in petroleum ether gave 4-carbomethoxycinnamaldehyde. Recrystallization from benzene gave 12.5 g 4-carbomethoxycinnamaldehyde, yield 73% m.p. 99°-101° C. The infrared spectrum showed absorption at 1720 cm-1 ##STR8## 1680 cm-1 (CHO), and 1620 cm-1 (--CH=CH--). NMR (CDCl3) showed δ3.8 (s, --COOCH3, 3) 6.5-7.1 (m,=CH--CHO, l), 7.3-7.6 (m, aromatic, 4), 7.9-8.1 (d, --CH=, l), and 9.8 (d, --CHO, l). Analysis calculated for C11H10O3 : C, 69.42%, H, 5.2%. Found: C, 68.69%, H, 5.25%. After evaporating toluene under reduced pressure the residue was chromatographed over silica column with 5% ethyl acetate in petroleum ether as eluant The second fraction obtained