Sodium hydride → Methyl 4-cyclopropyl-1H-pyrrole-3-carboxylate

HRID 1792818Notes

Reaction equation

HRID 1792818 reaction equation
C1(C)C=CC(S([CH2:10][N+:11]#[C-:12])(=O)=O)=CC=1.[CH:14]1([CH:17]=[CH:18][C:19]([O:21][CH3:22])=[O:20])[CH2:16][CH2:15]1.[H-].[Na+]>CS(C)=O.C(OCC)C.[Cl-].[Na+].O>[CH:14]1([C:17]2[C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:10][NH:11][CH:12]=2)[CH2:16][CH2:15]1

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 161915Tosylmethyl isocyanideHCID 5342132198272-33-4

Product 1

HCID 22024944Methyl 4-cyclopropyl-1H-pyrrole-3-carboxylateYield 86.1%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 8.77 g of p-toluenesulphonylmethyl isocyanide and 5.67 g of methyl 3-cyclopropylacrylate in 72 mL of dimethyl sulphoxide and 145 mL of diethyl ether is added dropwise over 1.5 hours and under an argon atmosphere to a suspension of 1.73 g (54 mmol) of sodium hydride (at 75% by weight in liquid petroleum jelly) in 90 mL of diethyl ether. The reaction is exothermic. After the reaction mixture has been stirred at room temperature for 2.75 hours, 180 mL of brine are added cautiously, and the mixture is extracted twice with 100 mL of diethyl ether. The organic phase is washed with water, dried and then concentrated to dryness under reduced pressure (2.7 kPa), giving 6.39 g of 4-cyclopropyl-3-methoxycarbonyl-1H-pyrrole in the form of a yellow solid melting at 107° C.

Workup

  1. extractionthe mixture is extracted twice with 100 mL of diethyl ether
  2. washThe organic phase is washed with water
  3. customdried
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-af3ceb1fa390416d870629c341924f90
Source dataset
uspto-grants-2006_07
Patent number
US07078414B2

Reaction notes

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