Phosphate → HCID 54568601, compound

Participants

Reaction Conditions

Reaction Steps

The alcohol 106 (147 mg, 0.791 mmol) was added to a suspension of NaH (60% in oil, 38 mg, 0.95 mmol, 1.2 equiv) in THF (5 mL). The resulting mixture was stirred at 25° C. for 30 min and cooled to 0° C. before CH3SO2Cl was added dropwise. The reaction mixture was stirred 15 min at 0° C. and 15 min at 25° C. Phosphate buffer (100 mL, pH 7) was added and the mixture extracted with CH2Cl2 (2×50 mL). The combined organic phase was dried (Na2SO4) and the solvent was removed under vacuum. Chromatography (SiO2, 2×25 cm, 30% EtOAc-hexane containing 2% Et3N) afforded 107 (205 mg, 208 mg theoretical, 98%) as a colorless oil as a mixture of E- and Z-olefin isomers (50:50): 1H NMR (CDCl3, 400 MHz) δ 6.24 (dt, J=12.3, 1.3 Hz, 0.5 H), 6.14 (dt, J=6.3, 1.4 Hz, 0.5H), 5.05 (dt, J=12.3, 7.5 Hz, 0.5H), 4.88 and 4.85 (two t, J=3.1, 3.4 Hz, 1H), 4.43 (m, 0.5H), 4.15 (m, 1H), 3.83 and 3.54 (two m, 2H), 3.05 (s, 3H), 2.17 and 1.98 (two m, 2H), 1.85-1.49 (m, 8H).

Provenance & Evidence