Water → Thiophene-2-sulfonic acid (2,4-difluoro-3-formyl-phenyl)-amide

HRID 250595Notes

Reaction equation

HRID 250595 reaction equation
[F:1][C:2]1[C:7]([CH2:8][OH:9])=[C:6]([F:10])[CH:5]=[CH:4][C:3]=1[NH:11][S:12]([C:15]1[S:16][CH:17]=[CH:18][CH:19]=1)(=[O:14])=[O:13].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.O>O1CCCC1>[F:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([F:10])[CH:5]=[CH:4][C:3]=1[NH:11][S:12]([C:15]1[S:16][CH:17]=[CH:18][CH:19]=1)(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 962WaterHCID 159087TriacetoxyperiodinaneHCID 58087783Thiophene-2-sulfonic acid (2,4-difluoro-3-hydroxymethyl-phenyl)-amide

Product 1

HCID 58086492Thiophene-2-sulfonic acid (2,4-difluoro-3-formyl-phenyl)-amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To thiophene-2-sulfonic acid (2,4-difluoro-3-hydroxymethyl-phenyl)-amide (511, 0.46 g, 1.52 mmol) in tetrahydrofuran (5.0 mL) was added Dess-Martin periodinane (0.71 g, 1.67 mmol). The reaction was stirred at room temperature for 10 minutes, then poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 20% ethyl acetate in hexane to give a white solid (512, 100 mg, 21%). MS (ESI) [M+H+]+=304.2.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by silica gel column chromatography
  6. washeluting with 20% ethyl acetate in hexane
  7. customto give a white solid (512, 100 mg, 21%)

Sources & evidence

ORD record
ord-3adab6b09e07461e982ccb43906cfbbb
Source dataset
uspto-grants-2011_01
Patent number
US07863288B2

Reaction notes

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