Dimethyl malonate → Dimethyl cyclopentane-1,1-dicarboxylate

HRID 217240

反応式

HRID 217240 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

HCID 12609605Dimethyl cyclopentane-1,1-dicarboxylate収率 82.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-f1910b2b9d6e45aa8fdb51f8d8baf472
出典データセット
uspto-grants-2012_06
特許番号
US08193349B2

関連ノート

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