反应详情

To a suspension of NaH (308 mg, 7.7 mmol, 60% in mineral oil) in dry THF (6 mL) under N2 atmosphere was added a solution of alcohol 7 (410 mg, 1.38 mmol) in THF (2 mL) while stirring for 30 min at room temperature. The reaction mixture was cooled to 0° C. and the compound 14 (crude 200 mg, 1.53 mmol) in THF (1 mL) was added dropwise and allowed to come to room temperature during a period of 30 min after which it was refluxed for 12 h. The mixture was quenched with ice water (5 mL), acidified to pH 2-3 by adding aqueous HCl solution (2N). The reaction mixture was extracted with CH2Cl2 (3×20 mL), washed with brine, dried over Na2SO4 and concentrated. The crude mass was taken in ethanol (10 mL), purged HCl gas for 30 min. and stirred at room temperature for 3 h. After evaporation of solvent, the crude mass was purified by column chromatography using 28% ethylacetate in hexane to furnish 14a (150 mg, 25%) as a white solid, mp-83.8-88.6° C.

1. temperatureThe reaction mixture was cooled to 0° C.
2. waitto come to room temperature during a period of 30 min
3. temperatureafter which it was refluxed for 12 h
4. customThe mixture was quenched with ice water (5 mL)
5. additionby adding aqueous HCl solution (2N)
6. extractionThe reaction mixture was extracted with CH2Cl2 (3×20 mL)
7. washwashed with brine
8. dry with materialdried over Na2SO4
9. concentrationconcentrated
10. custompurged HCl gas for 30 min.
11. stirringstirred at room temperature for 3 h
12. customAfter evaporation of solvent
13. customthe crude mass was purified by column chromatography