Isopropanol → HCID 86745099, compound

Participants

Reaction Steps

0.84 ml of a solution which is 3.25 molar in chromium trioxide and 5.29 molar in sulphuric acid is added dropwise at 0°-5° to a solution of 0.5 g of alcohol 8 according to h) in 15 ml of acetone. The mixture is stirred at 0° for 30 minutes and at room temperature for35 minutes, and then 4 ml of isopropanol, 80 ml of ethyl acetate and 30 ml of 20% sodium chloride solution are added thereto, and the mixture is filtered. The aqueous phase is extracted three times with 20 ml of ethyl acetate each time. The organic phase is dried over sodium sulphate and concentrated by evaporation. Chromatography on 20 g of silica gel using hexane/ethyl acetate/acetic acid 16:10:1 yields 0.34 g of 9, [α]D =-35.25° (c=1.39, CHCl3), --C-NMR (75 MHz, CDCl3): 173.8 (CO2H); 155.0 (OCON); 140.4 (C(4)); 121.1 (C(3)); 79.5 (OC(CH3)3); 70.3 (OCH); 52.1 (C(2)); 39.7 (d, J=18, C(5)); 28.3 ((CH3)3C); 25.7 (d, J=142, C(7)); 24.0 ((CH3)2CH); 20.2 (d, J=5, C(6)).

Provenance & Evidence