Hydrogen Peroxide → 3-Hexadecyloxy-2-triphenylmethoxymethylpropan-1-ol

Participants

Reaction Steps

A solution of compound 2 (5.00 g, 9.01 mmol) in 10 ml dry dioxane and BH3 -tetrahydrofuran (10 ml, 10.0 mmol) in tetrahydrofuran was stirred at room temperature for 2 hours. Water (10 ml) was added dropwise, followed by 2.5 N NaOH (20 ml) and 30% H2O2 (7.5 ml). The mixture was stirred at 50° for 2.5 hours, then was cooled and partitioned between CH2Cl2 and water. The aqueous layer was washed 3 times with CH2Cl2 and the combined extracts were dried over Na2SO4 and concentrated. Chromatography on silica gel using 10% ethyl acetatehexane afforded 3.37 g (66%) of the title compound (4) as a waxy white solid, m.p. 38°. NMR (CDCl3, (CH3)4Si); δ0.90 (t, 3H, J=6 Hz, --CH3), 1.25 (s, 26 H, --CH2 --), 1.54 (m, 2H, --OCH2CH2R), 2.16 (m, 1H, CH), 2.70 (t, 1H, J=6.5 Hz, --OH), 3.22 (d, 2H, J=6 Hz, CH2OTr), 3.41 (t, 2H, J=6 Hz, --OCH2R), 3.61 (t, 2H, J=6 Hz, CH2OR), 3.77 (t, 2H, J=6.5 Hz, CH2OH), 7.2-7.52 (m, 15H, C(C6H5)3).

Provenance & Evidence