Methanol--water (1/1) → 2-(4-Fluoro-3-methyl-benzenesulfonyl)-hexanoic acid methyl ester

HRID 1361051Notes

Reaction equation

HRID 1361051 reaction equation
C[O:2][C:3](=O)[CH:4]([S:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]([CH3:17])[CH:11]=1)[CH2:5][CH2:6][CH2:7][CH3:8].[OH:19]OS([O-])=O.[K+].[CH3:25][OH:26].[OH2:27]>O>[CH3:25][O:26][C:3](=[O:2])[CH:4]([S:9]([C:10]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]([CH3:17])[CH:11]=1)(=[O:19])=[O:27])[CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 22242641Methanol--water (1/1)HCID 23707502Potassium hydroxy sulfiteHCID 597751732-(4-Fluoro-3-methyl-phenylsulfanyl)-hexanoic acid methyl ester

Product 1

HCID 597752092-(4-Fluoro-3-methyl-benzenesulfonyl)-hexanoic acid methyl esterYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-(4-fluoro-3-methyl-phenylsulfanyl)-hexanoic acid methyl ester (0.160 g, 0.592 mmol) in 15 mL of MeOH/H2O (2:1), was added Oxone® (1.500 g, 1.776 mmol) in portions. After stirring at room temperature for 5 h, the reaction mixture was diluted with 60 mL of water and extracted with dichloromethane (60 mL×3). The organic extracts were combined and dried over anhydrous Na2SO4. After removing the solvent under reduced pressure, the product was isolated by Flash chromatography (silica gel) eluting with 0-30% ethyl acetate/hexanes to give the title compound as colorless semi-solid (0.153 g, 86% yield). LC-MS: tR=9.2 min; m/z 303 (M+H)+.

Workup

  1. extractionextracted with dichloromethane (60 mL×3)
  2. dry with materialdried over anhydrous Na2SO4
  3. customAfter removing the solvent under reduced pressure
  4. customthe product was isolated by Flash chromatography (silica gel)
  5. washeluting with 0-30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-95007c5cbfe447a181fb3e504600928b
Source dataset
uspto-grants-2011_02
Patent number
US07879911B2

Reaction notes

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