Water → HCID 59627881, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of compound 95 (50 mg, 0.152 mmol) in THF (1 ml) at 0° C. was added tetrabutylammonium fluoride (0.152 ml of 1 M solution in THF, 0.152 mmol) dropwise. The reaction mixture was stirred at 0° C. for 30 min and water (1 ml) and ethyl acetate (2 ml) were added. The layers were separated and the aqueous layer was extracted with ethyl acetate (2×2 ml). The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. Purification by flash column chromatography on silica (16-50% EtOAc/hexanes) afforded pure alcohol 96 (28 mg, 83%) as a white solid: [α]22D=−26.0 (c 0.3, CHCl3); TLC Rf=0.25 (silica gel, 50% EtOAc/hexanes); 1H NMR (600 MHz, CDCl3) δ 8.43 (s, 1H), 7.47-7.44 (dd, 1H, 3J=1.8 Hz, 2J=7.8 Hz), 7.19-7.17 (d, 1H, 3J==7.8 Hz), 6.0-5.95 (m, 1H), 5.12-5.17 (d, 1H, 3J=16.8 Hz), 5.09-5.06 (d, 1H, 3J=10.2 Hz), 4.48 (s, 1H), 2.96-2.91 (m, 1H), 2.69-2.60 (m, 2H), 2.32 (s, 3H), 2.03 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 153.62, 149.90, 140.25, 139.41, 136.65, 135.55, 131.19, 122.32, 115.43, 86.42, 52.26, 38.52, 18.49, 13.17; HRMS calcd for C14H17NO+Na+ 238.1208; found 238.1191 [M+Na+].

Provenance & Evidence