Water → HCID 68857927, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (4aR)-4a-allyl-7-methoxy-4,4a,9,10-tetrahydro-3H-phenanthren-2-one (15.0 grams, 55.9 mmol) in methylene chloride (350 mL) at −78° C. was added dropwise boron tribromide (10.6 mL, 112 mmol). The mixture was allowed to warm to 0° C. over 5 hours and was then poured onto a mixture of ice and water. Solid sodium bicarbonate was carefully added to neutralize the mixture which was then extracted with ethyl acetate. After washing with brine, the organic extract was dried (MgSO4) and concentrated under vacuum. The title compound (11.0 grams, 53%) was isolated by flash chromatography eluting with 5 to 10% ethyl acetate in methylene chloride. 1H NMR (CDCl3): δ 7.14 (d, J=8.5 Hz, 1 H), 6.72 (dd, J=2.7, 8.5 Hz, 1 H), 6.58 (d, J=2.7 Hz, 1 H), 5.94 (s, 1 H), 5.62–5.54 (m, 1 H), 5.03–4.98 (m, 2 H), 4.85 (br s, 1 H), 2.95–2.91 (m, 1 H), 2.85–2.63 (m, 5 H), 2.53–2.40 (m, 3 H), 2.08–1.99 (m, 1 H).

Provenance & Evidence