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

HRID 1348548ノート

反応式

HRID 1348548 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-422d960a922041c29902827a1bcca0d3
出典データセット
uspto-grants-2007_05
特許番号
US07211545B2

反応ノート

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