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

HRID 372961ノート

反応式

HRID 372961 の反応式
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

参加物

6

反応物 4

HCID 3283Diethyl Ether2 回HCID 24758Sodium hydrideHCID 161915Tosylmethyl isocyanideHCID 57087824,4,4-trifluorocrotononitrile

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-aeebcf87d9c94863852d6b28cc8ca3a4
出典データセット
uspto-grants-1992_11
特許番号
US05162308

反応ノート

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