Reaction #8873

Reaction equation

Bromomethylcyclopropane

sodium hydride

2-(diethoxyphosphoryl)acetic acid 4-methoxybenzyl ester

2-(Diethoxyphosphoryl)acetic acid para-methoxybenzyl ester

sodium bicarbonate

→

title compound

Yield 60.9%

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

Yield 60.9%

Solvents

diethyl ether

DMF

DMF

Conditions

Workup

1. 1
   workup.STIRRINGthe reaction mixture was stirred at room temperature for 12 h
2. 2
   Extractionextracted three times with diethyl ether
3. 3
   Washwashed with saturated sodium chloride
4. 4
   Dryingdried over sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   OtherThe volatiles were removed in vacuo
7. 7
   Otherthe residue was purified by FC (40% ethyl acetate in hexanes)

Procedure

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.

Source