Dimethyl malonate → Dimethyl cyclopentane-1,1-dicarboxylate

HRID 217240

반응식

HRID 217240 반응식
[CH3:1][O:2][C:3](=[O:9])[CH2:4][C:5]([O:7][CH3:8])=[O:6].Br[CH2:11][CH2:12][CH2:13][CH2:14]Br.C([O-])([O-])=O.[K+].[K+].F[B-](F)(F)F.C([N+]1C=CN(C)C=1)CCC>CN(C=O)C.O>[CH3:1][O:2][C:3]([C:4]1([C:5]([O:7][CH3:8])=[O:6])[CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:9]

참가 물질

7

반응물 4

HCID 7943Dimethyl malonateHCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 27341781-Butyl-3-methylimidazolium tetrafluoroborate

생성물 1

HCID 12609605Dimethyl cyclopentane-1,1-dicarboxylate수율 82.3%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of malonic acid dimethyl ester (5.28 g, 40 mmol) in DMF (100 ml), 1,4-dibromo-butane (5.26 ml, 44 mmol), K2CO3 (13.8 g, 100 mmol), 1-butyl-3-methylimidazolium tetrafluoroborate (0.904 g, 4.0 mmol) are added at room temperature. The mixture is stirred at room temperature for 15 hours. To the mixture, water is added and the solution is extracted with AcOEt. The organic layer is washed with H2O and brine, dried over MgSO4, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography to give cyclopentane-1,1-dicarboxylic acid dimethyl ester (6.13 g, 82%); TLC (hexane/AcOEt, 5:1) Rf 0.48, 1H NMR (400 MHz, chloroform-d) δ ppm 1.67-1.71 (m, 4H), 2.17-2.21 (m, 4H), 3.72 (s, 6H).

후처리

  1. extractionthe solution is extracted with AcOEt
  2. washThe organic layer is washed with H2O and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-f1910b2b9d6e45aa8fdb51f8d8baf472
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193349B2

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