Sodium hydride → Diethyl 2-(5-chloropentyl)-2-(4,4,5,5,5-pentafluoropentyl)malonate

HRID 460455ノート

反応式

HRID 460455 の反応式
[F:1][C:2]([F:21])([C:17]([F:20])([F:19])[F:18])[CH2:3][CH2:4][CH2:5][CH:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8].[H-].[Na+].Br[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][Cl:30]>CS(C)=O.O>[Cl:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][C:6]([CH2:5][CH2:4][CH2:3][C:2]([F:21])([F:1])[C:17]([F:18])([F:19])[F:20])([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:12]([O:14][CH2:15][CH3:16])=[O:13]

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 960701-Bromo-5-chloropentaneHCID 12017062Diethyl 2-(4,4,5,5,5-pentafluoropentyl)malonate

生成物 1

HCID 22718033Diethyl 2-(5-chloropentyl)-2-(4,4,5,5,5-pentafluoropentyl)malonate収率 83%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

実験手順

Diethyl 2-(4,4,5,5,5-pentafluoropentyl)malonate (3 g, 9.37 mmol) was dissolved in dimethyl sulfoxide (20 ml), and sodium hydride (60%, 525 mg, 13.11 mmol) was added to the resulting solution followed by stirring for 1 hour at room temperature. 5-Bromo-1-chloropentane (7.4 ml, 56.2 mmol) was added to the reaction mixture, followed by stirring for 1.5 hours at room temperature. The reaction mixture was diluted with water, extracted with ethyl acetate, washed with water and saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (eluent: dichloromethane/hexane=1/4) to give diethyl 2-(5-chloropentyl)-2-(4,4,5,5,5-pentafluoropentyl)malonate (3.3 g, Yield 83%) as a colorless oil.

後処理

  1. stirringby stirring for 1.5 hours at room temperature
  2. extractionextracted with ethyl acetate
  3. washwashed with water and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (eluent: dichloromethane/hexane=1/4)

出典と根拠

ORDレコード
ord-bb84b16c6dea4a6c80a62702895d8f3b
出典データセット
uspto-grants-2007_03
特許番号
US07196081B2

反応ノート

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