Cornforth reagent → HCID 11427434, compound

Participants

Reaction Steps

A mixture of 221 (3.26 g, 10.4 mmol) and pyridinium dichromate (14.0 g, 37.2 mmol) in DMF (45 mL) was stirred at room temperature for 46 h. The solution was diluted with 48% H2SO4 (30 mL) and water (300 mL) and extracted with ethyl acetate (5×100 mL). The combined organic layers were washed with saturated aqueous NaCl solution (5×100 mL), dried over anhydrous MgSO4, and concentrated in vacuo to give the crude product (3.19 g) as greenish oil. The crude product was subjected to column chromatography (silica gel; hexanes/ethyl acetate=3:1, 2:1), affording 223 (2.69 g, 79%) as a pale yellow oil. 1H NMR (CDCl3): δ 11.30 (br., 1 H), 4.10 (q, 2 H, J=7.2), 2.39 (t, 4 H, J=7.2), 1.56-1.48 (m, 8 H), 1.25-1.15 (m, 2 H), 1.24 (t, 3 H, J=7.2), 1.20 (s, 6 H), 1.15 (s, 6 H). 13C NMR (CDCl3): δ 210.9, 184.4, 178.1, 60.4, 43.1, 42.7, 42.2, 40.5, 39.8, 25.3, 25.0, 24.7, 24.3, 19.3, 14.4. HRMS (LSIMS, gly): Calcd for C18H33O5 (MH+): 329.2328, found: 329.2330.

Provenance & Evidence