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

HRID 1085609

Reaction equation

HRID 1085609 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-1b1378706cbd4f718dc061f916c71a29
Source dataset
uspto-grants-1991_04
Patent number
US05010098

Linked notes

Loading…