Methanesulfonyl chloride → 1-Hexadecyloxy-2-methanesulfonyloxymethyl-3-triphenylmethoxypropane

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Reaction Steps

Methanesulfonylchloride (0.752 g, 6.57 mmol) was added to a solution of 4 (3.00 g, 5.26 mmol) in dry pyridine (15 ml). After 3 hours the solution was poured into ice water and the product was extracted 3 times with hexane. The hexane extracts were washed with cold 1M H saturated NaHCO3 and water, and dried over Na2SO4 and concentrated. Chromatography on silica gel using hexane-CH2Cl2 (1:1 v/v) afforded 3.40 g (99%) the title compound (9) as a waxy solid, m.p. 39°. NMR (CDCl3, (CH3)4Si); δ0.90 (t, 3H, J=6 Hz, --CH3), 1.25 (s, 26H, --CH2 --), 1.52 (m, 2H, OCH2CH2R), 2.28 (m, 1H, CH), 2.84 (s, 3H, --CH3), 3.19, 3.21 (ABX, 2H, JAB = 10 Hz, /JAX +JBX /=8 Hz, CH2OTr, 3.35 (t, 2H, J=6.5 Hz, --OCH2R), 3.48 (d, 2H, J=6 Hz, CH2OR), 4.39 (d, 2H, J=6 Hz, CH2OMs).

Provenance & Evidence