Tetrahydrofuran → 4-(3-Fluorophenyl)-1H-pyrrole-3-carbonitrile

HRID 1629977노트

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HRID 1629977 반응식
[H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]#[N:13])[CH:7]=[CH:8][CH:9]=1.S([CH2:24][N+:25]#[C-])(C1C=CC(C)=CC=1)(=O)=O.O1CCC[CH2:28]1>C(Cl)(Cl)Cl>[F:3][C:4]1[CH:5]=[C:6]([C:10]2[C:11]([C:24]#[N:25])=[CH:12][NH:13][CH:28]=2)[CH:7]=[CH:8][CH:9]=1

참가 물질

6

반응물 4

HCID 8028Tetrahydrofuran2회HCID 24758Sodium hydrideHCID 161915Tosylmethyl isocyanideHCID 367315HCID 367315, 화합물2회

생성물 1

HCID 534262514-(3-Fluorophenyl)-1H-pyrrole-3-carbonitrile

시약·촉매·용매 1

HCID 6212Chloroform용매

반응 조건

온도
25 °C

실험 절차

To a suspension of 19.8 g (494 mmol) of sodium hydride at 60% in oil in 350 ml of anhydrous tetrahydrofuran is added dropwise a mixture of 48.5 g (330 mmol) of the mixture of (Z) and (E) 3-(3-fluorophenyl)-2-propenenitrile in a ratio of (7/3) and 64.4 g (330 mmol) of tosylmethyl isocyanide (CAS 36635-61-7) dissolved in 250 ml of tetrahydrofuran, while maintaining the temperature of the reaction medium at about 25° C. The mixture is then stirred for 1 hour at room temperature and is then poured into ice-water. The reaction product is then extracted with ethyl acetate, the organic phase is dried over sodium sulfate and the solvent is evaporated off under reduced pressure to give a brown solid, which is dissolved in 350 ml of hot chloroform and purified by chromatography on a column of 600 g of silica gel, eluting with dichloromethane and then with a mixture of 1% methanol in dichloromethane, to give 41.5 g of 4-(3-fluorophenyl)-1H-pyrrole-3-carbonitrile in the form of a beige-coloured solid after triturating in dichloromethane, filtering off and drying.

후처리

  1. additionis added dropwise
  2. extractionThe reaction product is then extracted with ethyl acetate
  3. dry with materialthe organic phase is dried over sodium sulfate
  4. customthe solvent is evaporated off under reduced pressure
  5. customto give a brown solid, which
  6. custompurified by chromatography on a column of 600 g of silica gel
  7. washeluting with dichloromethane
  8. additionwith a mixture of 1% methanol in dichloromethane

출처 및 근거

ORD 기록
ord-785abbf352e24392a0f78bdf588d55b0
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08791119B2

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