تفاعل #2348121

معادلة التفاعل

(4-Methoxybenzyl)triphenylphosphonium chloride

Sodium methoxide

Pyridinecarbaldehyde

→

trans-stilbene

المردود 61.8%

المذيبات

methanol

ظروف التفاعل

المعالجة

1. 1
   workup.WAITthe stirring was continued at room temperature overnight
2. 2
   أخرىExcess of sodium methoxide was quenched by addition of water and pH of the reaction mixture
3. 3
   workup.ADDITIONto pH=7.5-8.0 by addition of saturated sodium bicarbonate
4. 4
   استخلاصProducts were then extracted with ethyl acetate (500 mL)
5. 5
   غسيلCombined extracts were washed with water and brine
6. 6
   تركيزconcentrated in vacuo
7. 7
   أخرىThe crude product was purified by column chromatography

الإجراء التجريبي

(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.

المصدر