HCID 58100156, compound → HCID 58100069, compound

Participants

Reaction Steps

Pyrididium chlorochromate (7.32 g, 34.00 mmol) was added to a mixture of benzyl 4-[4-(4-hydroxypentyl)phenyl]butylcarbamate (138) (6.27 g, 17.00 mmol) and 4 Å molecular sieves in dichloromethane (250 mL) in three portions and stirred at rt for 6 h. The reaction mixture was then filtered through diatomaceous earth and the filtrate was concentrated to a black oil. Purification by column chromatography (silica, 30:70 ethyl acetate/hexanes) afforded ketone 140 (6.58 g, >99% yield) as a white solid: 1H NMR (500 MHz, CDCl3) δ 1.50-1.56 (m, 2H), 1.60-1.66 (m, 2H), 1.85-1.90 (m, 2H), 2.11 (s, 3H), 2.42 (t, 2H), 2.56-2.60 (m, 4H), 3.19-3.23 (m, 2H), 4.70 (br s, 1H), 5.08 (s, 2H), 7.07 (s, 4H), 7.29-7.36 (m, 5H).

Provenance & Evidence