Dimethylformamide → Tert-butyl 4-cyano-5-(methylsulfonyl)thiophene-2-carboxylate

HRID 448125Notes

Reaction equation

HRID 448125 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[S:6][C:7]=1SC)#[N:2].O[O:18][S:19]([O-:21])=O.[K+].[CH3:23]N(C)C=O>>[C:1]([C:3]1[CH:4]=[C:5]([C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])[S:6][C:7]=1[S:19]([CH3:23])(=[O:21])=[O:18])#[N:2]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 23707502Potassium hydroxy sulfiteHCID 66785900Tert-butyl 4-cyano-5-(methylthio)thiophene-2-carboxylate

Product 1

HCID 66785761Tert-butyl 4-cyano-5-(methylsulfonyl)thiophene-2-carboxylate

Procedure

A mixture of tert-butyl 4-cyano-5-(methylthio)thiophene-2-carboxylate (1.4 g, 5.5 mmol) and oxone (14.4 g, 21.5 mmol) in dimethylformamide (100 mL) was stirred at room temperature for 16 hours. The reaction mixture was then poured into ice/water (400 mL) and extracted with ethyl acetate. Organic layer was washed with water, dried over anhydrous sodium sulfate and evaporated to dryness to afford 1.5 g of the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. washOrganic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-1317688d90a547f98d124124dbb44bd3
Source dataset
uspto-grants-2013_07
Patent number
US08481584B2

Reaction notes

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