Ethanol → HCID 10221461, compound

Participants

Reaction Steps

Solid sodium tetraborohydride (NaBH4, 81 mg, 2.175 mmol) was added in one portion to a rapidly stirred solution of 176 (101 mg, 0.233 mmol) in a mixture of anhydrous EtOH (2 mL) and anhydrous THF (4 mL) at room temperature and allowed to stir for 4 h. The reaction mixture was diluted with water (5 mL) and extracted with CHCl3 (3×5 mL). The organic layers were washed with brine (10 mL) and dried over anhydrous MgSO4. Filtration and evaporation afforded the crude product, which was stirred for 30 minutes with silica gel (0.25 g) in MeOH (5 mL). Excess methanol was removed by rotary evaporation, causing the crude product to be absorbed onto the silica gel. The plug of silica gel was added to the top of a silica gel column and the product was purified by flash column chromatography eluting with a 60:40 mixture of petroleum ether:EtOAc. Pure fractions were combined and evaporation of the solvent in vacuo afforded the product (177) as a yellow solid (33 mg, 0.116 mmol, 50%). 1H NMR (270 MHz, CDCl3) δ7.86 (d, 1H, J=3.84 Hz, imine CH), 7.50 (s, 1H, ArH), 7.05 (br s, 1H, H3), 6.82 (s, 1H, ArH), 6.58 (dd, 1H, J=10.62, 17.22 Hz, alkene CH), 5.20-5.05 (m, 2H, alkene CH2), 4.39-4.31 (m, 1H, H11a), 3.96 (s, 3H, OMe), 3.94 (s, 3H, OMe), 3.39-3.12 (m, 2H, H1); 13C NMR (67.8 MHz, CDCl3) δ162.7, 161.5, 151.9, 147.8, 140.4, 129.9, 126.9, 123.9, 118.9, 114.4, 111.6, 109.8, 77.3, 56.2, 53.9, 33.7.

Provenance & Evidence