반응 #8873

반응 방정식

Bromomethylcyclopropane

sodium hydride

2-(diethoxyphosphoryl)acetic acid 4-methoxybenzyl ester

2-(Diethoxyphosphoryl)acetic acid para-methoxybenzyl ester

sodium bicarbonate

→

title compound

수율 60.9%

2-(Diethoxyphosphoryl)-3-cyclopropylproprionic acid 4-methoxybenzyl ester

수율 60.9%

용매

diethyl ether

DMF

DMF

반응 조건

후처리

1. 1
   workup.STIRRINGthe reaction mixture was stirred at room temperature for 12 h
2. 2
   추출extracted three times with diethyl ether
3. 3
   세척washed with saturated sodium chloride
4. 4
   건조dried over sodium sulfate
5. 5
   여과filtered
6. 6
   기타The volatiles were removed in vacuo
7. 7
   기타the residue was purified by FC (40% ethyl acetate in hexanes)

실험 절차

To a suspension of 60% sodium hydride in mineral oil (0.840 g, 21.0 mmol) in DMF (100 mL) was added a solution of 2-(diethoxyphosphoryl)acetic acid 4-methoxybenzyl ester (6.04 g, 19.1 mmol) from Step A in DMF (10 mL). The reaction mixture was stirred for 30 min at room temperature. Bromomethylcyclopropane (2.4 mL, 24.8 mmol) was added and the reaction mixture was stirred at room temperature for 12 h. The reaction mixture was diluted with diethyl ether, poured into saturated sodium bicarbonate, and extracted three times with diethyl ether. The organic layers were combined, washed with saturated sodium chloride, dried over sodium sulfate, and filtered. The volatiles were removed in vacuo and the residue was purified by FC (40% ethyl acetate in hexanes) to afford 4.31 g of the title compound.

출처