Sodium Bicarbonate → (1-Benzylcyclopropyl)methanol

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of the title B compound, 1-benzyl-cyclopropanecarboxylic acid tert-butyl ester (0.232 g, 1 mmol) in THF (8 mL) under nitrogen is added drop wise at −50° C. LiAlH4 (3 mL, 3 mmol, 1 m in THF). The resulting mixture is further stirred for 1 h at −50° C., then slowly allowed to reach room temperature and poured into a saturated NaHCO3 aqueous solution. The aqueous layer is extracted twice with EtOAc. and the combined organic extracts are dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue is purified by flash column chromatography on silica gel (hexane/EtOAc 4/1 to 1/1) to afford the title compound: TLC, Rf (hexane/AcOEt 1/1)=0.52. MS 180.0 [M+18]. Rt (HPLC, Nucleosil C18, 10:90-100:0 CH3CN/H2O+0.1% TFA within 5 min, then 100% CH3CN+0.1% TFA): 4.95 min.

Provenance & Evidence