Water → Propane-1-sulfonic acid (2-fluoro-3-formyl-phenyl)-amide

HRID 1397847Notes

Reaction equation

HRID 1397847 reaction equation
[F:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:10][S:11]([CH2:14][CH2:15][CH3:16])(=[O:13])=[O:12].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])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:10][S:11]([CH2:14][CH2:15][CH3:16])(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 962WaterHCID 159087TriacetoxyperiodinaneHCID 58087499Propane-1-sulfonic acid (2-fluoro-3-hydroxymethyl-phenyl)-amide

Product 1

HCID 58086814Propane-1-sulfonic acid (2-fluoro-3-formyl-phenyl)-amideYield 50.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To propane-1-sulfonic acid (2-fluoro-3-hydroxymethyl-phenyl)-amide (21, 0.20 g, 0.81 mmol) in 5.0 mL of tetrahydrofuran, Dess-Martin periodinane (0.377 g, 0.89 mmol) was added. 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 under vacuum and purified by silica gel column chromatography eluting with 20% ethyl acetate in hexane to give the desired compound as a white solid (22, 100 mg, 50.0%). MS(ESI) [M−H+]−=244.1.

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 under vacuum
  5. custompurified by silica gel column chromatography
  6. washeluting with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-c3686f91bc39465e9c9079b918d61cfb
Source dataset
uspto-grants-2014_12
Patent number
US08901301B2

Reaction notes

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