Butan-1-olate → Ethyl 2-(4,4,5,5,5-pentafluoro-1-oxopentyl)-9-decenoate

HRID 1792410ノート

反応式

HRID 1792410 の反応式
[F:1][C:2]([F:17])([C:13]([F:16])([F:15])[F:14])[CH2:3][CH2:4][C:5](=[O:12])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].[O-]CCCC.I[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH:30]=[CH2:31]>C1COCC1.[K]>[F:1][C:2]([F:17])([C:13]([F:14])([F:15])[F:16])[CH2:3][CH2:4][C:5]([CH:6]([CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH:25]=[CH2:24])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:12]

参加物

6

反応物 3

HCID 12476378Butan-1-olateHCID 138898108-Iodooct-1-eneHCID 22033121Ethyl 6,6,7,7,7-pentafluoro-3-oxoheptanoate

生成物 1

HCID 22033009Ethyl 2-(4,4,5,5,5-pentafluoro-1-oxopentyl)-9-decenoate

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 5462222Potassium溶媒

実験手順

To a stirred solution of ethyl 6,6,7,7,7-pentafluoro-3-oxoheptanoate (262 mg, 1 mmol) in anhydrous THF (4 ml), potassium tret-butoxide (112 mg, 1 mmol) was added as a solid and the mixture was stirred at room temperature for 30 min. Then to a solution of 8-iodo-1-octene (357 mg, 1.5 mmol) in anhydrous THF (1 ml) was added and the mixture was stirred at room temperature continued for 3 days. The mixture was concentrated, diluted with diethyl ether, washed with water, brine, dried over anhydrous sodium sulfate and concentrated in vacuum. Crude product was purified by flash chromatography on silica gel (hexane:ethyl acetate 10:1) to give ethyl 2-(4,4,5,5,5-pentafluoro-1-oxopentyl)-9-decenoate as a colorless oil. yield: 200 mg (54%).

後処理

  1. additionwas added as a solid
  2. stirringthe mixture was stirred at room temperature
  3. waitcontinued for 3 days
  4. concentrationThe mixture was concentrated
  5. additiondiluted with diethyl ether
  6. washwashed with water, brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuum
  9. customCrude product was purified by flash chromatography on silica gel (hexane:ethyl acetate 10:1)

出典と根拠

ORDレコード
ord-126b46c583eb4d38b98c533b7ad86f3c
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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