Diethyl Ether → HCID 66915011, compound

HRID 880427Notes

Reaction equation

HRID 880427 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[CH:7][C:8]([O-:10])=[O:9].C1(C)C(S([CH2:20][N+:21]#[C-:22])(=O)=O)=CC=CC=1.[H-].[Na+].[CH2:26](OCC)[CH3:27]>CS(C)=O>[CH2:26]([O:9][C:8]([C:7]1[C:6]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)=[CH:22][NH:21][CH:20]=1)=[O:10])[CH3:27]

Participants

6

Reactant 4

HCID 3283Diethyl Ether2×HCID 24758Sodium hydrideHCID 4113576HCID 4113576, compoundHCID 53627694Toluenesulfonylmethyl isocyanide

Product 1

HCID 66915011HCID 66915011, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of ethyl (3-(2-thienyl)prop-2-enoate (2.50 g, 13.70 mmol) and toluenesulfonylmethyl isocyanide (2.90 g, 14.90 mmol) in dimethylsulfoxide:diethyl ether (12.50 mL:20 mL) was added drop wise over a period of 15 min to a stirred solution of 60% sodium hydride in mineral oil (760 mg, 18.30 mmol) in diethyl ether (20 mL) at 10° C. Stirring was continued for 3 h at room temperature and the reaction mixture was quenched with saturated ammonium chloride solution and extracted with diethyl ether. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give crude compound which was purified by column chromatography over silica gel (100-200 mesh) using 18% ethyl acetate in pet ether as eluent to afford 4-thiophene-2-yl-1H-pyrrole-3-carboxylic acid ethyl ester (100 mg, 42%) as a solid.

Workup

  1. customthe reaction mixture was quenched with saturated ammonium chloride solution
  2. extractionextracted with diethyl ether
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give crude compound which
  7. customwas purified by column chromatography over silica gel (100-200 mesh)

Sources & evidence

ORD record
ord-fbc065f106234bbb8b493ffc48f42552
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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