Sodium Bicarbonate → (4-(Tert-butyldimethylsilyloxy)-3-ethoxyphenyl)methanol

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(tert-butyldimethylsilyloxy)-3-ethoxybenzaldehyde (12.7 g, 45.4 mmol, 1.0 equiv.) in EtOH (50 mL), NaBH4 (868 mg, 22.7 mmol, 0.5 equiv.) was added at 0° C., and the mixture was stirred at 0° C. for 2 h. After slow addition of sat. aq. NaHCO3-solution, the aqueous layer was extracted with EtOAc (2×). The combined organic phases were washed with brine, dried (MgSO4), filtered and the filtrate was concentrated to yield 12.6 g (98%) of (4-(tert-butyldimethylsilyloxy)-3-ethoxyphenyl)methanol as a light yellow oil.

Provenance & Evidence