反应详情

To a suspension of Intermediate 14a (2.28 g, 9.49 mmol) in EtOAc (25 mL) and aq. NaOH solution (1M, 23.7 mL, 23.7 mmol) was added 2,2,2-trichloroethyl chloroformate (1.57 mL, 11.4 mmol) dropwise over 2 min. A precipitate formed which redissolved after 15 min, then the orange solution was stirred at RT for 90 min. 2,2,2-Trichloroethyl chloroformate (0.391 mL, 2.85 mmol) was added, and the orange mixture stirred at RT for 16 h. The layers were separated, and the aqueous extracted with EtOAc (25 mL). The combined organics were washed with brine (25 mL), dried (Na2SO4), filtered and concentrated in vacuo to leave an orange-red oil. Recrystallisation from cyclohexane gave an off-white solid (3.12 g, 79%). LCMS (Method 3): Rt 4.46 min, m/z 415, 417 [MH+].

1. customA precipitate formed which
2. dissolutionredissolved after 15 min
3. stirringthe orange mixture stirred at RT for 16 h
4. customThe layers were separated
5. extractionthe aqueous extracted with EtOAc (25 mL)
6. washThe combined organics were washed with brine (25 mL)
7. dry with materialdried (Na2SO4)
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customto leave an orange-red oil
11. customRecrystallisation from cyclohexane