Water → 2-(1-Triethylsilanyloxy-cyclopentyl)-ethanol

Participants

Reaction Steps

1-Vinyl-1-triethylsilanyloxy-cyclopentane (9.06 g; 40.0 mmole) was dissolved in dry THF (100 ml); at 0° C. borane (1M in THF; 40.0 ml; 40.0 mmole) was added dropwise and the reaction mixture was stirred for one hour at ambient temperature. At 0° C. water (50 ml)was added dropwise, followed by NaBO3.4H2O (7.69 g; 50.0 mmole) and the mixture was stirred for additional 16 hours at ambient temperature; after filtration the organic layer was removed and concentrated in vacuo; the aqu. layer was extracted with tert.-BuOMe (2×50 ml); all organic layers were combined, washed with sat. aqu. NaCl (50 ml) and dried over MgSO4. After filtration the solvent was removed in vacuo, the crude product was chromatographed on silica gel (hexane:ethyl acetate--4:1). 2-(1-Triethylsilanyloxy-cyclopentyl)-ethanol (D1) was obtained as colourless oil.

Provenance & Evidence