Sodium hydride → HCID 66914869, compound

HRID 880430Notes

Reaction equation

HRID 880430 reaction equation
C1(C)C(S([CH2:10][N+:11]#[C-:12])(=O)=O)=CC=CC=1.[CH:14]1([CH:18]=[CH:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:17][CH2:16][CH2:15]1.[H-].[Na+]>CS(C)=O.C(OCC)C>[CH:14]1([C:18]2[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:10][NH:11][CH:12]=2)[CH2:15][CH2:16][CH2:17]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 53627694Toluenesulfonylmethyl isocyanideHCID 54090850HCID 54090850, compound

Product 1

HCID 66914869HCID 66914869, compoundYield 67.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent2×

Procedure

Toluenesulfonylmethyl isocyanide (3.04 g, 15.59 mmol) was added to the stirred solution of ethyl 3-cyclobutylprop-2-enoate (2.00 g, 12.99 mmol) in a mixture of dimethylsulfoxide (2 mL) and diethyl ether (30 mL) and stirred for 45 min. The resulting mixture was added to a slurry of sodium hydride (675 mg, 38.14 mmol, 60% in mineral oil) in diethyl ether (10 mL) over a period of 30 min then stirred for a further 1 h. The reaction mixture was quenched with saturated ammonium chloride solution, the organics were separated and the aqueous layer was extracted with diethyl ether (4×10 mL). The combined organic layer was washed with water, brine, dried over anhydrous sodium sulphate, filtered and concentrated. The residue was subjected to column chromatography over silica gel (100-200 mesh) using 0% to 15% of ethyl acetate in pet-ether as eluent, concentrated and dried under reduced pressure to afford ethyl 4-cyclobutyl-1H-pyrrole-3-carboxylate (1.70 g, 67%) as a liquid.

Workup

  1. stirringthen stirred for a further 1 h
  2. customThe reaction mixture was quenched with saturated ammonium chloride solution
  3. customthe organics were separated
  4. extractionthe aqueous layer was extracted with diethyl ether (4×10 mL)
  5. washThe combined organic layer was washed with water, brine
  6. dry with materialdried over anhydrous sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. concentrationconcentrated
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-d31ad3972f64403a8e73b4f9d914cf16
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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