Sulfuric Acid → Estra-1,3,5(10),16-tetraen-3-ol

Participants

Reaction Steps

This synthesis is depicted in FIG. 11. A solution of the ketone 10 (800 mg, 3.10 mmol) in dry ether (5 ml) was added dropwise at RT. to a slurry of LiAlH4 (38 mg, 1 mmol) in ether (3 ml) (e). After 1 h, the mixture was hydrolyzed with 10% aq. H2SO4. After workup (ether), the crude product (802 mg, 9:1-mixture of 12 and 11) was chromatographed on silica gel with CH2Cl2. A small fraction of 11 (70 mg) was eluted first, followed by the main fraction of 12 (705 mg, 87%). M.p. 113°-115°, [a]- +36.3° (C=1.0). - IR. (CHCl3): 3640 m, 3500 br., 1585w. -1H-NMR. (90 MHz) : 0.78 (s, 3 H); 3.60 (m, w1/2 ≈(m, 20, 1 H); 5.71 (m, 1 H), 5.87 (m, 1 H).

Provenance & Evidence