Ethanol → HCID 10221461, compound

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) δ 7.86 (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) δ 162.7, 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.

1. extractionextracted with CHCl3 (3×5 mL)
2. washThe organic layers were washed with brine (10 mL)
3. dry with materialdried over anhydrous MgSO4
4. filtrationFiltration and evaporation
5. customafforded the crude product, which
6. customExcess methanol was removed by rotary evaporation
7. customto be absorbed onto the silica gel
8. additionThe plug of silica gel was added to the top of a silica gel column
9. customthe product was purified by flash column chromatography
10. washeluting with a 60:40 mixture of petroleum ether
11. customevaporation of the solvent in vacuo

ORD record

ord-efc5f1541ce1404e83745a83e41c91d0

Source dataset

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07049311B1