Aluminium lithium hydride → HCID 10040611, compound

Participants

Reaction Steps

A solution of the diacetate (25) (25 mg, 0.065 mmol) in dry ether (1 ml) was added to a stirred solution of lithium aluminium hydride (5 mg, 0.13 mmol) in dry ether (2 ml) at 0° C. under argon. After 15 min, excess lithium aluminium hydride was destroyed by addition of wet ether and then dropwise addition of water. The ethereal layer was separated, dried, and evaporated, and the residue was chromatographed on silica (1 g) to give the product (6) (18 mg, 91%), m.p. 161°-2° C. (from ether-light petroleum), νmax 3420 cm-1 (OH), δ (250 MHz), 7.21 (1 H, d, J 8 Hz, 1-proton), 6.76 (1 H, dd, J 8 and 2.5 Hz, 2-proton), 6.67 (1 H, d, J 2.5 Hz, 4-proton), 4.74 (1 H, m, 11-proton), 3.78 (3 H, s, OCH3), 3.71 (1 H, m, 17-proton), 2.86 (2 H, m, 7-protons), 2.44 (1 H, dd, J 11 and 2 Hz, 9-proton), 2.28 (1 H, dd, J 14 and 2.5 Hz, 12-proton), 2.11 (1 H, qt, J 11, 9, 2.5, and 2 Hz, 8-proton), 1.98-1.31 (7 H, m), 1.61 (2 H, br s OH), 1.03 (3 H, s, 18-CH3);

Provenance & Evidence