Ethyl bromoacetate → 3-Cyano-3-(3,4-dimethylphenyl)pentanedioic acid diethyl ester

HRID 323229

反応式

HRID 323229 の反応式
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH3:11][C:12]1[CH:13]=[C:14]([CH2:19][C:20]#[N:21])[CH:15]=[CH:16][C:17]=1[CH3:18].Br[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25]>O1CCCC1.C(OCC)C>[CH2:27]([O:26][C:24](=[O:25])[CH2:23][C:19]([C:20]#[N:21])([C:14]1[CH:15]=[CH:16][C:17]([CH3:18])=[C:12]([CH3:11])[CH:13]=1)[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:28]

参加物

6

反応物 3

HCID 7748Ethyl bromoacetateHCID 764012-(3,4-Dimethylphenyl)acetonitrileHCID 2724254Sodium bis(trimethylsilyl)amide

生成物 1

HCID 538454283-Cyano-3-(3,4-dimethylphenyl)pentanedioic acid diethyl ester

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Cool a solution of sodium bis(trimethylsilyl)amide (723 mL, 1 M in tetrahydrofuran, 723 mmol) to 0° C. in an ice bath. Add a solution of 3,4-dimethylphenylacetonitrile (50.0 mmol) in tetrahydrofuran (130 mL) over about 1.5 hours. When the addition is complete, warm the reaction mixture to ambient temperature and allow to stir. After 2 hours, transfer the above solution via cannula into a cooled (−50° C.) solution of ethyl bromoacetate (126 g, 757 mmol) in tetrahydrofuran (250 mL). After the transfer is complete, allow the reaction mixture to warm to ambient temperature. After 18 hours, dilute with diethyl ether (500 mL) and extract with water, 1 M hydrochloric acid solution, saturated aqueous solution of sodium bicarbonate, and then brine. Dry the organic layer over MgSO4, filter, and concentrate in vacuo to give a residue. Recrystallize the residue from diethyl ether to give the title compound as a solid.

後処理

  1. additionWhen the addition
  2. temperatureto warm to ambient temperature
  3. waitAfter 18 hours
  4. extractionextract with water, 1 M hydrochloric acid solution, saturated aqueous solution of sodium bicarbonate
  5. dry with materialDry the organic layer over MgSO4
  6. filtrationfilter
  7. concentrationconcentrate in vacuo
  8. customto give a residue
  9. customRecrystallize the residue from diethyl ether

出典と根拠

ORDレコード
ord-15f6fc9b68d24231854cb21da8558d8c
出典データセット
uspto-grants-2001_04
特許番号
US06211199B1

関連ノート

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