2-Pyridinecarboxaldehyde → trans-Stilbene

(4-Methoxybenzyl)triphenylphosphonium chloride (4.79 g, 11.4 mmol) was suspended in 50 mL of dry methanol. Sodium methoxide (4.94 g of 25% solution in methanol, 22.8 mmol) was added in one portion to the above suspension and the resulting mixture was stirred at room temperature under nitrogen for 30 minutes. Pyridinecarbaldehyde (1.57 g, 11.4 mmol) was then added and the stirring was continued at room temperature overnight. Excess of sodium methoxide was quenched by addition of water and pH of the reaction mixture was adjusted to pH=4.5 with 1 N HCl, and then to pH=7.5-8.0 by addition of saturated sodium bicarbonate. Products were then extracted with ethyl acetate (500 mL). Combined extracts were washed with water and brine, and concentrated in vacuo. The crude product was purified by column chromatography using ethyl acetate in hexane (5%-10%) to give 1.27 g (46%) of trans-stilbene.

1. waitthe stirring was continued at room temperature overnight
2. customExcess of sodium methoxide was quenched by addition of water and pH of the reaction mixture
3. additionto pH=7.5-8.0 by addition of saturated sodium bicarbonate
4. extractionProducts were then extracted with ethyl acetate (500 mL)
5. washCombined extracts were washed with water and brine
6. concentrationconcentrated in vacuo
7. customThe crude product was purified by column chromatography

ORD record

ord-d4c608bd9ac74a3689fe472ee8408713

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08242144B2