Hydrochloric Acid → 2-((Tert-butyldimethylsilyl)oxy)acetaldehyde

Participants

Reaction Conditions

Reaction Steps

Under nitrogen and with stirring, 4.71 ml of oxalyl chloride were dissolved in 120 ml of dichloromethane and the solution was cooled to -70° C. Over 12 minutes while maintaining the temperature at -65° C., a solution of 8 ml of dimethylsulfoxide and 26 ml of dichloromethane was introduced. Then, after 10 minutes of contact at this temperature, a solution of 8.81 g of the product of Step A, 50 ml of dichloromethane and 8.86 ml of pyridine was added over 12 minutes at -65° C. After 15 minutes of contact at this temperature, 35 ml of triethylamine were added over 8 minutes at -65° C. At +13° C., the pH was adjusted to 4 by adding N hydrochloric acid. After decanting, re-extracting with 50 ml of dichloromethane, drying the organic phase and distilling under reduced pressure, the crude product obtained was chromatographed over silica and eluted with dichloromethane to obtain 7.95 g of 2-[(1,1-dimethylethyl)dimethylsilyloxy]-acetaldehyde.

Provenance & Evidence