Benzyl 4-formylbenzoate → 4-[(Dimethoxy-phosphoryl)-hydroxy-methyl]-benzoic acid benzyl ester

Reaction equation

[CH2:1]([O:8][C:9](=[O:18])[C:10]1[CH:15]=[CH:14][C:13]([CH:16]=[O:17])=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[P:19]([O-:24])([O:22][CH3:23])[O:20][CH3:21]>C1COCC1.CCOC(C)=O>[CH2:1]([O:8][C:9](=[O:18])[C:10]1[CH:11]=[CH:12][C:13]([CH:16]([P:19]([O:22][CH3:23])([O:20][CH3:21])=[O:24])[OH:17])=[CH:14][CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Procedure

A solution of 4-formyl-benzoic acid benzyl ester (0.50 g, 2.08 mmol) in THF (2.0 mL) was cooled to 0° C., then dimethyl phosphite (0.25 g, 2.29 mmol) and N,N,N′M′-tetramethyl-guanidine (0.02 g, 0.21 mmol) was added dropwise. The reaction mixture was warmed to ambient temperature. After stirring for 45 mins the reaction mixture was diluted with EtOAc and washed with 1N aqueous HCl (2×), brine, then dried (MgSO4) and concentrated in vacuo to give the title compound: MS: cal'd 351 (MH+), exp 351 (MH+)