Hydrochloric Acid → Ethyl (2-chloro-6-fluorophenyl)acetoacetate

HRID 1348548노트

반응식

HRID 1348548 반응식
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:5]=1[CH2:11][C:12]([O:14]CC)=O.[C:17]([O:20][C:21](=O)[CH3:22])(=[O:19])[CH3:18].Cl>O1CCCC1>[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:5]=1[CH2:11][C:12](=[O:14])[CH2:18][C:17]([O:20][CH2:21][CH3:22])=[O:19]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 24758Sodium hydrideHCID 2733231Ethyl 2-chloro-6-fluorophenylacetate

생성물 1

HCID 63022492Ethyl (2-chloro-6-fluorophenyl)acetoacetate수율 35.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Into a mixture of 9.6 g of sodium hydride (60% in oil) and 200 ml of tetrahydrofuran, 21.7 g of ethyl 2-chloro-6-fluorophenylacetate were added dropwise under reflux. Then, a solution of 12.3 g of acetic anhydride in 40 ml tetrahydrofuran was added thereto and refluxed under heating for 10 hours. The reaction mixture was cooled, poured into iced dil. hydrochloric acid and extracted with t-butyl methyl ether. The organic layer was washed with dil. hydrochloric acid, aqueous saturated sodium bicarbonate solution, dil. hydrochloric acid and water, subsequently, dried over sodium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give 9.27 g of ethyl (2-chloro-6-fluorophenyl)acetoacetate.

후처리

  1. additionwere added dropwise
  2. temperatureunder reflux
  3. temperaturerefluxed
  4. temperatureunder heating for 10 hours
  5. temperatureThe reaction mixture was cooled
  6. extractionextracted with t-butyl methyl ether
  7. washThe organic layer was washed with dil. hydrochloric acid, aqueous saturated sodium bicarbonate solution, dil. hydrochloric acid and water
  8. dry with materialsubsequently, dried over sodium sulfate
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-422d960a922041c29902827a1bcca0d3
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07211545B2

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