Water → HCID 21864426, compound

Participants

Reaction Steps

The 1α-hydroxy-38-triethylsilyloxy-compound from Example 9(b) (2 g) was treated with benzoyl chloride (2 ml) in pyridine (25 ml). After 30 min water was added and the mixture diluted with ether. After acid work-up, the solvent was removed and the resulting oil stirred overnight in THF:H2O: AcOH; 8:1:3 (36 ml). After dilution with ether and aqueous work-up, the crude benzoate-alcohol was taken up in benzene (40 ml). Triethylamine (7 ml), acetic anhydride (3 ml) and 4-dimethylaminopyridine (15 mg) were added. After 30 min, water was added and the mixture diluted with ether. Acid work-up and chromatography through silica (10 g) gave 1.76 g 83%) of the title acetate-benzoate as an oil. 1Hnmr δ 8.05 (m. W=12 Hz, 2H, aryl), 7.5 (m, W=10 Hz, 3H, aryl), 6.58 (d, J=11 Hz, C-6H), 5.88 (m, W=16 Hz, C-1H, 7H), 5.15 (m, W=10 Hz, C-3H, 19H2, 22H, 23H), 2.05 (s, OAc), 0.57 (s, C-18H3).

Provenance & Evidence