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

HRID 1582804노트

반응식

HRID 1582804 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-b091cfb2821d4c13a8615b34387cc47c
출처 데이터셋
uspto-grants-2004_05
특허 번호
US06737417B2

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