Diethyl Ether → HCID 69046303, compound

Participants

Reaction Steps

Compound 6 was dissolved in 30 mL of anhydrous ether and 10 mL of anhydrous pyridine. A solution of silver acetate (1.03 g, 1(914 mg, 2.98 mmol) in 5 mL of anhydrous pyridine was added. The reaction mixture was stirred under dark for 0.5 hr. A heavy greenish precipitate was deposited. Ether (50 mL) was added and precipitate was filtered off. The filtrate was under vacuum to dryness. The residue was purified by flash chromatograph on silica gel eluted with 50:50 ethyl acetate:hexanes to afford the title compound 7 (124 mg) as a white solid. Selected 1H NMR data: (CD3OD, 300 MHz): δ 5.78 (d, 1H, J=2.2 Hz), 5.34 (br, 1H), 4.02 (t, 1H, J=4.5 Hz), 3.52 (dt, 1H, J=7.7 Hz, 3.0 Hz), 3.37 (d, 1H, J=4.9 Hz), 2.03 (s, 3H), (1.12 (s, 3H), 0.75 (s, 3H). Melting Point: 152-153° C.

Provenance & Evidence