Ethanol → Ethyl 6-[(4,4,5,5,5-pentafluoropentyl)oxy]hexanoate

HRID 459684ノート

反応式

HRID 459684 の反応式
CC1C=CC(S([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])(=O)=O)=CC=1.[F:22][C:23]([F:32])([C:28]([F:31])([F:30])[F:29])[CH2:24][CH2:25][CH2:26]O.CC(C)([O-])C.[K+].C(O)C>O1CCCC1>[F:22][C:23]([F:32])([C:28]([F:31])([F:30])[F:29])[CH2:24][CH2:25][CH2:26][O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]

参加物

6

反応物 4

HCID 702EthanolHCID 5479674,4,5,5,5-Pentafluoropentan-1-olHCID 11056130Hexanoic acid, 6-[[(4-methylphenyl)sulfonyl]oxy]-, ethyl esterHCID 23665647Potassium tert-butoxide2 回

生成物 1

HCID 18444112Ethyl 6-[(4,4,5,5,5-pentafluoropentyl)oxy]hexanoate収率 19.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
200 °C

実験手順

To a stirred solution of the product of step (a) (500 mg) and 4,4,5,5,5-pentafluoropentan-1-ol (284 mg) in tetrahydrofuran (10 ml) was added potassium tert-butoxide (1M in tetrahydrofuran; 1.6 ml) and the reaction was stirred at 200° C. for 2 hours. An additional charge of potassium tert-butoxide (1M in tetrahydrofuran; 1.6 ml) was added and the reaction was stirred for a further 18 hours. Ethanol (5 ml) was added and the reaction was stirred for 30 mlnutes. The reaction mixture was partitioned between dichloromethane (300 ml) and water (300 ml). The organic layer was dried over magnesium sulphate and the solvent was removed in vacuo. Purification by column chromatography on silica gel (5 g Bond Elut cartridge) eluting with 20% ethyl acetate in cyclohexane gave the title compound as a clear oil (100 mg).

後処理

  1. additionwas added
  2. stirringthe reaction was stirred for a further 18 hours
  3. stirringthe reaction was stirred for 30 mlnutes
  4. customThe reaction mixture was partitioned between dichloromethane (300 ml) and water (300 ml)
  5. dry with materialThe organic layer was dried over magnesium sulphate
  6. customthe solvent was removed in vacuo
  7. customPurification by column chromatography on silica gel (5 g Bond Elut cartridge)
  8. washeluting with 20% ethyl acetate in cyclohexane

出典と根拠

ORDレコード
ord-5fc9b9c0de2443bb91b34f635e0d3e32
出典データセット
uspto-grants-2007_03
特許番号
US07195752B2

反応ノート

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