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

HRID 48111

反応式

HRID 48111 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-487cb1cdebea42d59d94f98259f552fc
出典データセット
uspto-grants-2004_03
特許番号
US06703082B1

関連ノート

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