Ethyl Acetate → HCID 13686452, compound

Participants

Reaction Steps

To the solution of the acetate (7) (92 mg, 0.198 mmol) in pyridine (2 ml) was added dropwise phosphorusoxychloride (0.06 ml) at 0° and the mixture was stirred at room temperature for 2 hr. To the reaction mixture were added ice and ethyl acetate. The organic phase was washed with 2N-HCl, saturated NaHCO3 and brine, and dried over MgSO4. The residue obtained upon evaporation of the solvent was purified by column chromatography on silica gel (5 g). Elution with benzene-ethyl acetate (20:1) gave the olefine (8) (90 mg, 98%), mp 116°-119° (MeOH); δ0.68(3H s, 18H3), 0.87(6H, d, J=6 Hz, 26- and 27-H3), 0.93(3H, d, J=6 Hz, 21-H3), 1.06(3H, s, 19-H3), 2.08(3H, s, acetyl), 4.10-5.00(1 H, broad, 2β-H), 4.86(1H, m, 3α-H), and 5.42(1H, m, 6-H); m/z 386.3370(M+ -AcOH). (CH27H43F required M, 386.3347).

Provenance & Evidence