반응 #1881817
ord-8b824e212b134e3a8a96087bbc9118ee
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후처리
- 1기타prepared
- 2workup.ADDITIONthis suspension was added dropwise to the above suspension under ice cooling
- 3workup.STIRRINGthe mixture was stirred at room temperature for 15 hr
- 4추출the mixture was extracted with ethyl acetate
- 5세척The ethyl acetate layer was washed with a saturated aqueous sodium hydrogencarbonate solution and saturated brine
- 6건조was then dried over anhydrous sodium sulfate
- 7기타The solvent was then removed by evaporation under the reduced pressure
- 8기타The crude product thus obtained
- 9기타was purified on Wako Gel
- 10세척(200 ml; elution solvent=n-hexane-ethyl acetate (10:1))
실험 절차
In ml of tetrahydrofuran was suspended 96 mg of 60% sodium hydride. The mixture of 2-ethyl-3-methyl-4-hydroxy-6-fluoro-7-chloroquinoline with 2-ethyl-3-methyl-4-hydroxy-5-chloro-6-fluoroquinoline (starting material 1) (480 mg) prepared as described in Example 6 was suspended in 10 ml of tetrahydrofuran, and this suspension was added dropwise to the above suspension under ice cooling. After stirring for one hr, 300 mg of isopropyl chloroformate (starting material 2) was added thereto, and the mixture was stirred at room temperature for 15 hr. The reaction solution was poured into water, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated aqueous sodium hydrogencarbonate solution and saturated brine and was then dried over anhydrous sodium sulfate. The solvent was then removed by evaporation under the reduced pressure. The crude product thus obtained was purified on Wako Gel C-200 (200 ml; elution solvent=n-hexane-ethyl acetate (10:1)) to give 345.1 mg of 2-ethyl-3-methyl-4-isopropoxycarbonyloxy-6-fluoro-7-chloroquinoline (compound 22) and 170.7 mg of 2-ethyl-3-methyl-4-isopropoxycarbonyloxy-5-chloro-6-fluoro -quinoline (compound 23). 1H-NMR data are shown in Table 3.