Tetrabutylammonium Fluoride → (1S,2S)-2-Hydroxy-2-methyl-3-cyclopentene-1-methanol

Participants

Reaction Steps

To a solution of (1S,5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-1-methylcyclopent-2-en-1-ol (560 mg, 1.53 mmol) in THF (29.5 mL) at 0° C. was added 1.00 M of tetra-n-butylammonium fluoride in THF (3.06 mL, 3.06 mmol). The mixture was stirred at rt for 2 h, at which point the solvent was concentrated in vacuo and the residue was purified by silica gel chromatography eluting with a gradient of 50 to 100% EtOAc in hexanes to afford the title compound (181 mg, 92%). LC/MS: Rt=0.76 min, ES+ 129 (AA standard).

Provenance & Evidence