Sodium Thiosulfate → HCID 59248869, compound

Participants

Reaction Steps

Anhydrous dichloromethane (2 mL) was used to solubilize 1-(5-iodooxazol-2-yl)-7-(3-methoxyphenyl)heptan-1-ol (0.050 g, 0.120 mmol) under an atmosphere of argon with stirring. Dess-Martin periodinane (0.076 g, 0.181 mmol) was added and the reaction was allowed to proceed over 1 hour at ambient temperature. The reaction was then worked up with saturated sodium bicarbonate. Saturated sodium thiosulfate was added and the organic phase was separated. The organic phase was washed with brine and dried over sodium sulfate. The solvent was removed under reduced pressure and the product (60%, 0.030 g) was purified by preparative thin layer chromatography with silica (30% ethyl acetate:hexanes mobile phase) as a yellow oil: 1H NMR (600 MHz, CDCl3) δ 7.33 (s, 1H), 7.18 (m, 1H), 6.75 (d, J=7.2 Hz, 1H), 6.71 (m, 2H), 3.79 (s, 3H), 3.02 (t, 2H), 2.57 (t, 3H), 1.71-1.76 (m, 2H), 1.60-1.65 (m, 2H), 1.35-1.44 (m, 4H); 13C NMR (150 MHz, CDCl3) δ 187.11, 162.53, 159.53, 144.27, 137.40, 129.15, 120.80, 114.12, 110.85, 93.61, 55.09, 38.63, 35.87, 31.09, 28.91 (2 C), 23.75; HRMS (ES+) m/e calc'd for [M+H]+ C17H21INO3: 414.0561. found 414.0560.

Provenance & Evidence