Methanol → 2-((Tert-butyldimethylsilyl)oxy)acetaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of 32.7g (0.15 mole) of ethyl t-butyldimethylsilyloxyacetate in 924 ml of methylene chloride a solution of 1M diisopropylaluminum hydride in methylene chloride is added dropwise with stirring at -78° C. over a period of 1/2 h. The mixture is stirred for 45 min and 100 ml of methanol is added dropwise. The mixture is diluted with 3 l of ether, 100 ml of brine and 70 g of sodium sulfate are added and the mixture is stirred at room temperature for 15 h. The solids are filtered, the filtrates are evaporated and the residue is distilled to give t-butyldimethylsilyloxyacetaldehyde, b.p. 65°-75° C. (14 mm/Hg).

Provenance & Evidence