Water → Dimethyl(2-oxo-4-phenylbutyl)phosphonate

Participants

Reaction Steps

To a solution of 68 g of methyl-phosphonic-acid dimethyl ester (MW=124.8; 1.6 eq.) in 325 mL of THF was added 218 mL of n-hexyllithium (2.5M in hexane; 1.6 eq.) at −80° C. The mixture was stirred for 30 min and a solution of 60 g of ethyl-3-phenyl propionate (MW=178.23, d=1.01, 1.0 eq.) in 90 mL of THF was added. The mixture was allowed to warm to ambient temperature and 150 mL of water were added. After separation of the layers the organic layer was extracted twice with water. The pH value of the combined aqueous layers was adjusted to pH=2 with 5M HCl and then extracted twice with DCM. Removal of the organic solvents under reduced pressure gave 89 g of the title compound (Assay: 86.8%; Yield=89.7%). It is not necessary to dry to completion, a 50 w % solution in MED is also suitable for the next step.

Provenance & Evidence