TBAF tetrahydrofuran → HCID 57814824, compound

Participants

Reaction Steps

A solution of silyl ether 14 (316 mg, 0.50 mmol) was stirred at 35° C. with 2 mL of 1.0M TBAF/THF in a vial for 9.5 h. TLC indicated starting material was mostly desilylated and the reaction was concentrated in vacuo. The residual crude products were taken up in 50 mL of ethyl acetate and washed sequentially with saturated ammonium chloride (50 mL), brine (50 mL), and dried over 10 g of anhydrous sodium sulfate. The mixture was filtered and concentrated in vacuo. The residual products were purified by flash column chromatography on 40 g of silica gel eluted in 1:1 hexanes:EtOAc, then straight EtOAc. Combination of appropriate fractions and removal of the solvents yielded 218 mg (84%) of diol 15 as an oil; 1H NMR (CDCl3): 0.94 (t, J=7.5 Hz, 31H), 1.18 (d, J=6.3 Hz, 3H), 1.31 (m, 6H), 1.42-1.90 (m, 19H), 2.10-2.50 (m, 7H), 3.48 (m, 1H), 3.72-4.16 (m, 7H), 4.64 (dt, 1H), 5.57 (m, 2H).

Provenance & Evidence