Tetrabutylammonium Fluoride → HCID 66959677, compound

Participants

Reaction Steps

A solution of TBS protected alcohol 47 (110 mg, 0.24 mmol) in THF (5 mL) was treated with TBAF (250 mL, 0.25 mmol). After stirring overnight the reaction was extracted with ethyl acetate (25 mL), the organics washed with water and brine, dried and evaporated. The resultant pale yellow oil was purified by column chromatography (2% methanol in chloroform) to give the desired diol 48 as a clear colourless oil (65 mg) which showed δH 6.78 (1H, s, ArH), 6.64 (1H, s, ArH), 5.51 (1H, s, OH), 3.86 (3H, s, OMe), 3.40-3.68 (5H, m, 2×OCH2 and CHOR), 2.72-2.82 (2H, m, 6-CH2), 1.20-2.30 (14H, m) and 0.81 (3H, s, 18-Me); δC 144.6, 143.5, 131.7, 129.5, 114.6, 109.1, 89.4, 70.9, 62.1, 56.1, 50.2, 44.2, 38.6, 38.0, 28.9, 28.1, 27.2, 26.6, 23.0 and 11.7.

Provenance & Evidence