Malononitrile → Methyl 3-(dicyanomethyl)tetrahydrofuran-3-carboxylate

HRID 1615944

反応式

HRID 1615944 の反応式
[H-].[Na+].[C:3](#[N:7])[CH2:4][C:5]#[N:6].Br[C:9]1([C:14]([O:16][CH3:17])=[O:15])[CH2:13][CH2:12][O:11][CH2:10]1.C(=O)([O-])O.[Na+]>C1COCC1>[C:5]([CH:4]([C:3]#[N:7])[C:9]1([C:14]([O:16][CH3:17])=[O:15])[CH2:13][CH2:12][O:11][CH2:10]1)#[N:6]

参加物

6

反応物 4

HCID 8010MalononitrileHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 66653660Methyl 3-bromotetrahydrofuran-3-carboxylate

生成物 1

HCID 86689276Methyl 3-(dicyanomethyl)tetrahydrofuran-3-carboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

440 mg (11.00 mmol) of sodium hydride (60% in mineral oil) were initially charged in 30 ml of THF, and 726 mg (11.00 mmol) of malononitrile were added in portions. Thereafter, 2.3 g (11.00 mmol) of the compound obtained in example 11A in THF (50 ml) were added. The mixture was stirred at RT for 6 h and then heated to 50° C. overnight. After cooling, the mixture was admixed with saturated aqueous sodium hydrogencarbonate solution and extracted three times with ethyl acetate. The combined organic phases were washed with saturated aqueous sodium chloride solution and then dried over sodium sulfate, filtered and concentrated. The residue (2.66 g) was dried under high vacuum for 1 h and then converted without further purification.

後処理

  1. temperatureheated to 50° C. overnight
  2. temperatureAfter cooling
  3. extractionextracted three times with ethyl acetate
  4. washThe combined organic phases were washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. dry with materialThe residue (2.66 g) was dried under high vacuum for 1 h
  9. customconverted without further purification

出典と根拠

ORDレコード
ord-9e968955856e4e3fabd83b50d7d5a609
出典データセット
uspto-grants-2014_07
特許番号
US08765769B2

関連ノート

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