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

HRID 1651697

반응식

HRID 1651697 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 3283Diethyl Ether용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7afcc8742b304d3893d682373928c3ba
출처 데이터셋
uspto-grants-1990_05
특허 번호
US04929634

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