Sodium hydride → ethyl 4-(4-chlorophenyl)-1H-pyrrole-3-carboxylate

HRID 1085609

反応式

HRID 1085609 の反応式
[H-].[Na+].[Cl:3][C:4]1[CH:16]=[CH:15][C:7]([CH:8]=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:5]=1.C1(C)C=CC(S([CH2:26][N+:27]#[C-:28])(=O)=O)=CC=1>CCOCC.O>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:8]2[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:26][NH:27][CH:28]=2)=[CH:15][CH:16]=1

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 161915Tosylmethyl isocyanideHCID 2014712-Propenoic acid, 3-(4-chlorophenyl)-, ethyl ester

生成物 1

HCID 470434ethyl 4-(4-chlorophenyl)-1H-pyrrole-3-carboxylate収率 25.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒2 回

実験手順

To a mixture of 5.63 g of a 60% sodium hydride/oil suspension in 200 mL of dry ether under nitrogen is added from an additional funnel a mixture of 23.5 g (122 mmol) of ethyl p-chlorocinnamate and 19.4 g (122 mmol) of (p-tolylsulfonyl)methyl isocyanide in solution in 180 mL of ether and 80 mL of dimethylsulfonide. The addition time is about 20 minutes and results in gentle refluxing of the mixture. After another 10 minutes stirring, the mixture is diluted with 100 mL of water. The mixture is extracted four times with ether which is then dried over magnessium sulfate followed by concentrated in vacuo. The resulting solid is recrystallized from ethylene dichlorite to give 7.8 g of crystals, m.p. 137°-138° C.

後処理

  1. additionis added from an additional funnel
  2. customresults
  3. temperaturein gentle refluxing of the mixture
  4. extractionThe mixture is extracted four times with ether which
  5. dry with materialis then dried over magnessium sulfate
  6. concentrationby concentrated in vacuo
  7. customThe resulting solid is recrystallized from ethylene dichlorite

出典と根拠

ORDレコード
ord-1b1378706cbd4f718dc061f916c71a29
出典データセット
uspto-grants-1991_04
特許番号
US05010098

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