Triethylamine → 1-{[Tert-butyl(dimethyl)silyl]oxy}-5-chloro-3-phenylpentan-3-ol

Participants

Reaction Conditions

Reaction Steps

To a 0° C. solution of 5-chloro-3-phenylpentane-1,3-diol (4.3 g, 20 mmol) and Et3N (3.4 mL, 24 mmol) in 20 mL DMF, was added tert-butyldimethylsilyl chloride (3.3 g, 21 mmol). After stirring for 2 h at 0° C., the reaction mixture was diluted with EtOAc, washed with saturated aqueous NaHCO3, dried (Na2SO4) and chromatographed (9:1 hex:EtOAc) to provide 1-{[tert-butyl(dimethyl)silyl]oxy}-5-chloro-3-phenylpentan-3-ol (5.2 g, 79%) as a clear oil. 1H NMR (400 MHz, CDCl3): δ 7.40-7.32 (m, 4H), 7.25 (m, 1H), 4.88 (s, 1H), 3.73 (dt, 1H, J=10.3, 4.0 Hz), 3.65 (ddd, 1H, J=11.5, 10.6,5.1 Hz), 3.44 (td, 1H, J=10.6, 2.7 Hz), 3.15 (ddd, 1H, J=11.3, 10.6, 5.1 Hz), 2.34 (ddd, 1H, J=13.3, 11.4, 5.1 Hz), 2.27-2.15 (m, 2H), 1.96 (dt, 1H, J=14.6, 3.2 Hz), 0.86 (s, 9H), −0.02 (s, 3H), −0.09 (s, 3H); ESI-MS 351 (M+Na).

Provenance & Evidence