Isopropanol → HCID 86745097, compound

Participants

Reaction Steps

To a solution of 1.6 g of alcohol 2 according to b) in 60 ml of acetone there are added at 0°-5° 3.3 ml of a solution that is 3.25 molar in chromium(VI) oxide and 5.29 molar in sulphuric acid. The mixture is stirred at 0° for 6 hours and at room temperature for 12 hours. After the addition of 5 ml of isopropanol and 40 ml of 20% sodium chloridesolution, the mixture is stirred for 10 minutes and is then extracted continuously with methyl acetate for 15 hours in a Kutscher-Steudel apparatus. The organic phase is dried over sodium sulphate and concentrated by evaporation, and the residue is chromatographed on 75 g ofsilica gel with hexane/ethyl acetate/acetic acid 16:10:1. This yields 0.92 g of 3, [α]D =-94.5° (c=1.2, CHCl3). 1H-NMR (300 MHz, CDCl3): 1.2-1.3 (4d, (2-propo)2); 1.4 (s, (CH3)3CO); 1.95 (d, J=3, CH3 --C(4)); 3.5 and 3.62 (2 d×d, J=23 and 15, 2H--C(5)); 4.66 (m, (2-propo)2); 4.92 (m, H--C(2)); 5.30 (m, H--C(3)); 5.42 (d, J=7, NH); 9.0-10.0 (broad, CO2H).

Provenance & Evidence