反应详情

温度

85 °C

To a stirred suspension of 6α-carboxyandrostane-3,17-dione (II-aq, Prepn. 17, 600 mg) in dry toluene (12 mL), SOCl2 (623 μL) was added. After stirring 5.5 h at 85° C. the solution was cooled at 0° C. and 2M NH3 solution in MeOH (2.97 mL) was added. After stirring overnight at room temperature, the mixture was evaporated to dryness. The residue was treated with CH2Cl2 and H2O and extracted with CH2Cl2. The combined organic extracts were washed with 10% K2CO3 solution, brine, dried over Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography (SiO2, n-hexane/acetone 50/50) to give the title compound II-ar (90 mg, 15%). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 7.27 (bs, 1H), 6.78 (bs, 1H), 2.50-0.72 (m, 21H), 1.00 (s, 3H), 0.80 (s, 3H).

1. additionwas added
2. temperaturewas cooled at 0° C.
3. stirringAfter stirring overnight at room temperature
4. customthe mixture was evaporated to dryness
5. additionThe residue was treated with CH2Cl2 and H2O
6. extractionextracted with CH2Cl2
7. washThe combined organic extracts were washed with 10% K2CO3 solution, brine
8. dry with materialdried over Na2SO4
9. customevaporated to dryness
10. customThe residue was purified by flash chromatography (SiO2, n-hexane/acetone 50/50)