Diethyl Ether → 1H-Pyrrole-3-carbonitrile, 4-(trifluoromethyl)-

HRID 372961노트

반응식

HRID 372961 반응식
C1(C)C=CC(S([CH2:10][N+:11]#[C-])(=O)=O)=CC=1.[H-].[Na+].[CH:16](/[C:22]#[N:23])=[CH:17]\[C:18]([F:21])([F:20])[F:19].[CH2:24](OCC)C>CS(C)=O>[F:19][C:18]([F:21])([F:20])[C:17]1[C:16]([C:10]#[N:11])=[CH:22][NH:23][CH:24]=1

참가 물질

6

반응물 4

HCID 3283Diethyl Ether2회HCID 24758Sodium hydrideHCID 161915Tosylmethyl isocyanideHCID 57087824,4,4-trifluorocrotononitrile

생성물 1

HCID 151507031H-Pyrrole-3-carbonitrile, 4-(trifluoromethyl)-

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

A mixture of p-tolylsulfonylmethylisocyanide (0.72 g, 3.2 mmol) and sodium hydride (0.09 g, 3.8 mmol) in anhydrous ethyl ether is treated dropwise with a solution of 4,4,4-trifluorocrotonitrile (0.38 g, 3.2 mmol) in ether and dimethyl sulfoxide over a 35 minute period, stirred at room temperature for 20 minutes and quenched with water. The phases are separated and the aqueous phase is extracted with ether. The organic phases are combined, washed with brine, dried over MgSO4 and concentrated in vacuo to afford an orange solid residue. The residue is flash chromatographed using silica gel and 100:100:1 petroleum ether: ethyl ether: acetic acid followed by 100% methylene chloride to give the title product as a white solid, mp 96°-97° C.

후처리

  1. customquenched with water
  2. customThe phases are separated
  3. extractionthe aqueous phase is extracted with ether
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto afford an orange solid residue
  8. customchromatographed

출처 및 근거

ORD 기록
ord-aeebcf87d9c94863852d6b28cc8ca3a4
출처 데이터셋
uspto-grants-1992_11
특허 번호
US05162308

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