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

HRID 908890Notes

Reaction equation

HRID 908890 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 give 1.5 g of the title compound. Chromatographic method A, Rf 6.2; [M+H]+ 288.

Workup

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

Sources & evidence

ORD record
ord-f5b1e1af58ec484dbdcf9c2e3088c8d0
Source dataset
uspto-grants-2011_09
Patent number
US08017643B2

Reaction notes

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