Cornforth reagent → HCID 86762465, compound

Participants

Reaction Steps

PDC (2.1 g, 5.6 mmol) was added to a stirred mixture of alcohol 7 (1.72 g, 5.6 mmol) and activated 4 Å molecular sieves (1.0 g) in anhydrous dichloromethane (20 mL). The resulting mixture was stirred for 5 h; then it was diluted with diethyl ether (20 mL). The resulting suspension was filtrated through a pad of silica gel. The solvent was removed in vacuo and the residue was purified by column chromatography on silica gel (hexanes/ethyl acetate=5:1) to provide aldehyde 6 (1.46 g, 4.8 mmol) as a white solid in 85% yield: m.p.: 153-154° C.; IR (thin film): 3272, 1691, 1609, 1544, 1504, 1257, 1206 cm−1; 1H NMR (500 MHz, CDCl3): δ 10.01 (s, 1H), 7.93-7.81 (m, 5H), 7.68 (d, J=8.2 Hz, 1H), 7.57 (s, 1H), 7.55-7.40 (m, 4H), 5.32 (s, 2H) ppm; 13C NMR (101 MHz, CDCl3): δ 192.07, 192.03, 154.26, 143.05, 136.09, 134.16, 132.34, 130.94, 130.08, 128.82, 128.28, 126.74, 126.41, 126.20, 125.83, 125.47, 120.68, 119.36, 66.35 ppm. HRMS (m/z): [M+Na]+ calcd. for C19H15NNaO3, 328.0944; found, 328.0938.

Provenance & Evidence