Sodium hydride → Ethyl 4-methyl-1h-pyrrole-3-carboxylate

HRID 1419136Notes

Reaction equation

HRID 1419136 reaction equation
[C:1]([O:6][CH2:7][CH3:8])(=[O:5])/[CH:2]=[CH:3]/[CH3:4].C1(C)C=CC(S([CH2:18][N+:19]#[C-:20])(=O)=O)=CC=1.[H-].[Na+]>CCOCC.CS(C)=O.CCOCC.O>[CH3:4][C:3]1[C:2]([C:1]([O:6][CH2:7][CH3:8])=[O:5])=[CH:18][NH:19][CH:20]=1

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 161915Tosylmethyl isocyanideHCID 429065Ethyl trans-crotonate

Product 1

HCID 235044Ethyl 4-methyl-1h-pyrrole-3-carboxylateYield 80.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 19869614Ether dimethylsulfoxideSolvent

Procedure

A solution of 11.86 g (0.1 moles) of ethyl crotonate and 19.50 g (0.1 moles) of p-toluenesulfonylmethylisocyanide in 500 mL of a 2:1 ether/dimethylsulfoxide was added dropwise into a suspension of 6.8 g of sodium hydride (60% mineral oil dispension, 0.17 moles) in ether at room temperature. Upon completion of addition the reaction mixture was stirred for 30 min and diluted with 400 mL of water. The aqueous layer was extracted with 3×100 mL of ether. The combined ether extracts were passed through a column of alumina eluting with dichloromethane. The organic solvent was evaporated and the resulting residue was solidified on standing. The solid was washed with hexane and dried at 40° C. in vacuum oven overnight to yield 12.38 g (80%) of the title compound.

Workup

  1. additionUpon completion of addition the reaction mixture
  2. extractionThe aqueous layer was extracted with 3×100 mL of ether
  3. customThe organic solvent was evaporated
  4. washThe solid was washed with hexane
  5. customdried at 40° C. in vacuum oven overnight

Sources & evidence

ORD record
ord-6f4b30c2ff0940868fc994b493001ab4
Source dataset
uspto-grants-1999_03
Patent number
US05886020

Reaction notes

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