Hexane → HCID 68638963, compound

Participants

Reaction Conditions

Reaction Steps

A 1 molar solution of tetrabutylammonium fluoride in tetrahydrofuran (27 mL, 1.3 equiv) was added to a stirred solution of silyl ether 52 (6.7 g, 20 mmol, 1.0 equiv) in tetrahydrofuran (80 mL) at 25° C. The resulting brown solution was stirred at 25° C. for 3 h. The reaction mixture was concentrated by rotary evaporation. The residue was purified by silica gel column chromatography (25% hexane in ethyl acetate) to afford S5 (4.4 g, 99% yield) as a brown oil. Rf=0.44 (25% hexane in ethyl acetate); 1H NMR (500 MHz, C6D6) δ 5.37 (t, 1H, J=1 Hz, CHCCl), 4.79 (dd, 1H, J=0.5, 5.5 Hz, CH(OR)), 4.23 (dd, 1H, J=1, 5.5 Hz, CH(OR)), 3.64 (d, 1H, J=11 Hz, CH2(OH)), 3.37 (d, 1H, J=11 Hz, CH2(OH)), 1.23 (s, 3H, CH3), 1.07 (d, 3H, J=0.6 Hz, CH3); 13C NMR (125 MHz, C6D6) δ 139.51, 130.65, 113.46, 85.82, 85.33, 83.12, 65.29, 27.29, 26.08; IR (neat film) 3401 (m), 2989 (w), 2937 (w), 1624 (w) cm−1; HRMS (ESI) m/z: Calcd for C9H13ClNaO4 (MNa+) 243.0400, observed 243.0412.

Provenance & Evidence