反应详情

To a solution of trans-methyl 4-(chloro(hydroxyimino)methyl)cyclohexanecarboxylate (5.90 g, 26.9 mmol) and isopropenyl acetate (53.8 g, 537 mmol) in dichloromethane (134 ml) was added triethylamine (5.44 g, 53.7 mmol) at 0-5° C. The cooling bath was removed 15 minutes after completed addition, and the mixture was stirred for 20 h. The reaction mixture was concentrated in vacuo. The residue was partitioned between ethyl acetate (250 ml) and 0.1 M aqueous hydrochloric acid solution (200 ml). The organic layer was washed with one 100 ml-portion of 0.1 M aqueous hydrochloric acid solution. The combined aqueous layers were extracted with one 150 ml-portion of ethyl acetate. The combined organic layers were washed with one 200 ml-portion of 2 M sodium carbonate and one 100-ml portion of brine, dried over anhydrous sodium sulfate and concentrated in vacuo. Purification with n-heptane/ethyl acetate as eluent gave the title compound (3.00 g, 50%) as off-white solid. MS m/e: 224 ([M+H]+)

1. customThe cooling bath was removed 15 minutes
2. additionaddition
3. concentrationThe reaction mixture was concentrated in vacuo
4. customThe residue was partitioned between ethyl acetate (250 ml) and 0.1 M aqueous hydrochloric acid solution (200 ml)
5. washThe organic layer was washed with one 100 ml-portion of 0.1 M aqueous hydrochloric acid solution
6. extractionThe combined aqueous layers were extracted with one 150 ml-portion of ethyl acetate
7. washThe combined organic layers were washed with one 200 ml-portion of 2 M sodium carbonate and one 100-ml portion of brine
8. dry with materialdried over anhydrous sodium sulfate
9. concentrationconcentrated in vacuo
10. customPurification with n-heptane/ethyl acetate as eluent