Ethyl Acetate → Ethyl 6,6,7,7,7-pentafluoro-3-oxoheptanoate

HRID 1792408ノート

反応式

HRID 1792408 の反応式
[C:1]([O:4][CH2:5][CH3:6])(=[O:3])[CH3:2].C[Si](C)(C)[N-][Si](C)(C)C.[Na+].[F:17][C:18]([F:28])([C:24]([F:27])([F:26])[F:25])[CH2:19][CH2:20][C:21](Cl)=[O:22]>C1COCC1>[F:17][C:18]([F:28])([C:24]([F:25])([F:26])[F:27])[CH2:19][CH2:20][C:21](=[O:22])[CH2:2][C:1]([O:4][CH2:5][CH3:6])=[O:3]

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 220330904,4,5,5,5-Pentafluoropentanoyl chloride

生成物 1

HCID 22033121Ethyl 6,6,7,7,7-pentafluoro-3-oxoheptanoate収率 56%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of ethyl acetate enolate, prepared from ethyl acetate (4.4 g, 50 mmol) and sodium hexamethyldisilazide (50 mmol) in THF at −70° C., was added neat 4,4,5,5,5-pentafluoropentanoyl chloride (2.1 g, 10 mmol) at −70° C. Cooling bath was removed and the reaction mixture was allowed to warm to room temperature. The mixture was diluted with diethyl ether and quenched with water. The organic layer was separated, washed with aqueous 2 N hydrochloric acid, saturated sodium bicarbonate solution, brine, dried over anhydrous sodium sulfate and concentrated in vacuum. The crude product was purified by flash chromatography on-silica gel (hexane ethyl acetate 5:1) to give ethyl 6,6,7,7,7-pentafluoro-3-oxoheptanoate as colorless oil yield: 1.46 g (56%).

後処理

  1. temperatureCooling bath
  2. customwas removed
  3. additionThe mixture was diluted with diethyl ether
  4. customquenched with water
  5. customThe organic layer was separated
  6. washwashed with aqueous 2 N hydrochloric acid, saturated sodium bicarbonate solution, brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuum
  9. customThe crude product was purified by flash chromatography on-silica gel (hexane ethyl acetate 5:1)

出典と根拠

ORDレコード
ord-c9a8b8dff5a04d489160160a139b1a41
出典データセット
uspto-grants-2006_07
特許番号
US07074819B2

反応ノート

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