Dimethyl Sulfoxide → HCID 86747150, compound

Participants

Reaction Conditions

Reaction Steps

A solution of oxalylchloride (0.6 g, 6.7 mmol) in 20 mL methylene chloride is cooled to -70° C. Dimethylsulfoxide (0.6 mL, 8.4 mmol) is added dropwise. The solution is warmed to -30° C. then cooled to -70° C. A solution of diethyl [[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-(hydroxymethyl)phenyl]methyl]phosphonate (1.73 g, 4.45 mmol) from Preparation 18 in methylenechloride (15 mL) is added to the reaction mixture. The reaction mixture is stirred for 0.5 hours then warmed to -35° C. Triethylamine (4.7 mL, 33.5 mmol) is added and the mixture allowed to warm to room temperature. Methylenechloride (400 mL) is added and the organic phase is washed with 100 mL H2O. The organic phase is dried (MgSO4) and concentrated. The residue is passed through a 200-g silica gel plug using 5% MeOH/CH2Cl2 as the eluent. An oil of diethyl [[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-formylphenyl]methyl]phosphonate is obtained (1.67 g, 97%).

Provenance & Evidence