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0 °C

A solution of benzyl 2-((methoxyphosphinyl)methyl)-4-phenylbutanoate (4.02 g, 11.6 mmol) in methanol (20 mL) was cooled in an ice bath and 2.5N aqueous sodium hydroxide (5.1 mL. 12.8 mmol) was added over 10 min. The resulting solution was stirred at 0° C. for 45 min before being diluted with water (150 mL) and washed with a mixture of ether (75 mL) and hexane (25 mL). The aqueous layer was washed with hexane (75 mL), acidified by the addition of 2N aqueous hydrochloric acid (20 mL), and extracted with ethyl acetate (2×75 mL). The ethyl acetate layers were washed in succession with saturated aqueous sodium chloride (50 mL), dried (sodium sulfate), decanted, and evaporated. The residue was dried overnight under vacuum to give crude (±)-benzyl 2-((hydroxyphosphinyl)methyl)-4-phenylbutanoate as 3.67 g of colorless oil (95% yield).

1. washwashed with a mixture of ether (75 mL) and hexane (25 mL)
2. washThe aqueous layer was washed with hexane (75 mL)
3. additionacidified by the addition of 2N aqueous hydrochloric acid (20 mL)
4. extractionextracted with ethyl acetate (2×75 mL)
5. washThe ethyl acetate layers were washed in succession with saturated aqueous sodium chloride (50 mL)
6. dry with materialdried (sodium sulfate)
7. customdecanted
8. customevaporated
9. customThe residue was dried overnight under vacuum