Diethyl Ether → [Ethoxy(4-phenylbutyl)phosphoryl]acetic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-phenylbutyl phosphonous acid, ethyl ether (0.5 g, 0.0022 mole) in chloroform (10 ml) was added triethylamine (0.68 ml, 0.0048 mole) and the solution was cooled in an ice bath to 0° C. Trimethyl silyl chloride (0.6 ml, 0.0048 mole) was added to the above solution dropwise, followed by bromoacetic acid (0.34 g, 0.0024 mole). The ice bath was removed and the mixture stirred at room temperature for 5 hours and poured into 10% aqueous HCl (30 ml) and crushed ice (20 g). After shaking the mixture in a separatory funnel, the chloroform layer was separated and the aqueous layer extracted with dichloromethane (2×50 ml). The combined organic phase was washed with brine, dried over anhydrous sodium sulfate and the solvents removed on a rotavap. The resulting crude thick oil was vacuum dried to get 0.61 g (97%) of title compound in the form of an oil, TLC: Silica gel, CH2Cl2 :MeOH:HOAc shows one main spot at Rf =0.37.

Provenance & Evidence