Acetone → HCID 52919351, compound

Participants

Reaction Steps

Jone's reagent was added dropwise to a stirred solution of 17Z,20Z,23Z,26Z)-12-(phenylsulfonyl)dotriaconta-17,20,23,26-tetraen-1-ol (1 M solution in THF, 0.764 mL, 0.764 mmol) dissolved in acetone (5 mL) till the completion of reaction (TLC monitoring). The reaction was quenched with methanol (2 mL) and stirred for 30 min. The solvent was then removed and the crude was purified by silica gel column chromatography using 30% ethyl acetate/hexane to furnish the title compound as a clear oil (0.0643, 84%). 1H NMR (CDCl3): δ7.88 (d, 2H, J=7.2 Hz), 7.60 (m, 3H), 5.36 (m, 8H), 2.79 (m, 7H), 2.27 (t, 2H, J=6.8 Hz), 2.07 (m, 4H), 1.68 (m, 2H), 1.37-1.20 (m, 28H), 1.04 (t, 3H, J=6.8 Hz). m/z (APCI) 613.45 (M++1).

Provenance & Evidence