Ethyl Acrylate → 4-(5,5,6,6,7,7,8,8,8-Nonafluoro-octyl)-cyclohex-3-enecarboxylic Acid Ethyl Ester

HRID 48111

반응식

HRID 48111 반응식
[Cl-].[Al+3].[Cl-].[Cl-].[F:5][C:6]([F:25])([C:15]([F:24])([F:23])[C:16]([F:22])([F:21])[C:17]([F:20])([F:19])[F:18])[CH2:7][CH2:8][CH2:9][CH2:10][C:11]([CH:13]=[CH2:14])=[CH2:12].[C:26]([O:30][CH2:31][CH3:32])(=[O:29])[CH:27]=[CH2:28]>C1(C)C=CC=CC=1>[CH2:31]([O:30][C:26]([CH:27]1[CH2:28][CH2:12][C:11]([CH2:10][CH2:9][CH2:8][CH2:7][C:6]([F:25])([F:5])[C:15]([F:23])([F:24])[C:16]([F:21])([F:22])[C:17]([F:18])([F:19])[F:20])=[CH:13][CH2:14]1)=[O:29])[CH3:32]

참가 물질

5

반응물 3

HCID 8821Ethyl AcrylateHCID 6451240Aluminum(III) ChlorideHCID 206321542-(5,5,6,6,7,7,8,8,8-Nonafluoro-octyl)-buta-1,3-diene

생성물 1

HCID 867593684-(5,5,6,6,7,7,8,8,8-Nonafluoro-octyl)-cyclohex-3-enecarboxylic Acid Ethyl Ester수율 88%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a slurry of aluminum chloride (0.1 equi) in toluene (1 mL/mmole), ethyl acrylate (1 equi.) (1 equi.) was added at ice temperature. The reaction mixture was stirred at ice temperature for 10 min. Then a solution 2-(5,5,6,6,7,7,8,8,8-nonafluoro-octyl)-buta-1,3-diene (40) (0.5M in THF) (1 equi.) was added at ice temperature over a period of 20 min. The reaction mixture was stirred at ice temperature for 10 h, water, extracted with hexane, washed with brine, dried over MgSO4, and concentrated in vacuo. Purification by chromatography on silica gel (hexanes) gave 4-(5,5,6,6,7,7,8,8,8-nonafluoro-octyl)-cyclohex-3-enecarboxylic acid ethyl ester (41) as a colorless oil (88%).

후처리

  1. stirringThe reaction mixture was stirred at ice temperature for 10 h
  2. extractionwater, extracted with hexane
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification by chromatography on silica gel (hexanes)

출처 및 근거

ORD 기록
ord-487cb1cdebea42d59d94f98259f552fc
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06703082B1

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