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

HRID 1615944

반응식

HRID 1615944 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9e968955856e4e3fabd83b50d7d5a609
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765769B2

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