Tetrabutylammonium Fluoride → 1-Hexadecyloxy-2-fluoromethyl-3-triphenylmethoxypropan

Participants

Reaction Steps

A solution of 9 (1.10 g, 1.70 mmol) and tetrabutylammonium fluoride (2.00 g, 7.60 mmol) in dry N,N-dimethylformamide was stirred under N2 at 60°. After 18 hours, the solution was concentrated and the residue was partitioned between hexane and water. The hexane layer was washed 3 times with water, dried over Na2SO4 and concentrated. Chromatography on silica gel using hexane-CH2Cl2 (1:1, v/v) afforded 0.871 g (87%) of the title compound (10) as a colorless wax, m.p. 32°. NMR (CDCl3, --(CH3)4Si); δ0.90 (t, 3H, J=6 Hz, --CH3), 1.25 (s, 26H, --CH2 --), 1.55 (m, 2H, --OCH2CH2R), 2.32 (d of septets, 1H, JH--H =6 Hz, JH--F =23.5 Hz, --CH), 3.19 (d, 2H, J=6.0 Hz, --CH2OTr), 3.36 (t, 2H, J=6.5 Hz, --OCH2R), 3.49 (d, 2H, J=6.0 Hz, --CH2OR), 4.59 (d of d, 2H, JHH =6.0 Hz, JH--F =47.5 Hz, --CH2F), 7.2-7.52 (m, 15H, --C(C6H5)3)

Provenance & Evidence