Ethyl Acetate → Tert-butyl 3-hydroxy-2,2-dimethylpropanoate

Participants

Reaction Steps

1M lithium tri-tert-butoxy-aluminohydride/tetrahydrofuran solution (14 ml) was added dropwise to a solution of tert-butyl methyl 2,2-dimethyl-malonate (1.12 g) in tetrahydrofuran (30 ml) under nitrogen atmosphere over 15 minutes and the mixture was heated to reflux for 2 hours. The reaction mixture was cooled to room temperature, a saturated ammonium chloride aq. solution and ethyl acetate were added and the organic layer was separated, washed with water and a saturated brine, dried over magnesium sulfate and concentrated in vacuo to give the titled compound (800 mg). MS (m/z): 175 [M+H]+.

Provenance & Evidence