Ethyl Acetate → HCID 68527740, compound

Participants

Reaction Steps

2-(1-(tert-Butyl dimethylsilyloxy)-7-(3-methoxyphenyl)heptyl)-5-iodooxazole (0.088 g, 0.166 mmol) was dissolved in tetrahydrofuran (2 mL) under an atmosphere of argon with stirring and 1 M tetrabutylammonium fluoride (in tetrahydrofuran) (0.199 mL, 0.199 mmol) was added. The reaction was allowed to proceed over 90 minutes before dilution with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. The solvent was removed in vacuo and the desired product was purified as an oily white solid in 88% yield (0.061 g) using flash column chromatography with silica (0-30% ethyl acetate:hexanes gradient mobile phase): 1H NMR (500 MHz, CDCl3) δ 7.17-7.20 (m, 1H), 7.07 (s, 1H), 6.76 (d, J=7.5 Hz), 6.72 (m, 2H), 4.77 (q, 1H), 3.79 (s, 3H), 3.24 (bs, 1H), 2.57 (t, 2H), 1.80-1.93 (m, 2H), 1.58-1.62 (m, 2H), 1.43-1.48 (m, 1H), 1.30-1.42 (m, 5H); 13C NMR (150 MHz, CDCl3) δ 170.52, 159.48, 144.32, 135.05, 129.11, 120.79, 114.13, 110.80, 110.74, 86.84, 67.48, 55.07, 35.89, 35.21, 31.16, 29.03 (2 C), 24.84; HRMS (ES+) mile calc'd for [M+H]+ C17H23INO3: 416.0717. found 416.0699.

Provenance & Evidence