Methanesulfonic Acid → HCID 59153172, compound

HRID 2355267Notes

Reaction equation

HRID 2355267 reaction equation
CS(O)(=O)=O.C([O:13][C:14]1[C:19]([C:20]([F:23])([F:22])[F:21])=[C:18]([O:24]CC2C=CC=CC=2)[CH:17]=[CH:16][C:15]=1[C:32](=[O:37])[CH2:33][CH:34]([CH3:36])[CH3:35])C1C=CC=CC=1>CSC>[OH:13][C:14]1[C:19]([C:20]([F:21])([F:22])[F:23])=[C:18]([OH:24])[CH:17]=[CH:16][C:15]=1[C:32](=[O:37])[CH2:33][CH:34]([CH3:35])[CH3:36]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 59153174HCID 59153174, compound

Product 1

HCID 59153172HCID 59153172, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 1068Dimethyl SulfideSolvent

Procedure

Add methanesulfonic acid (41 mL) to a solution of 1-(2,4-bis-benzyloxy-3-trifluoromethyl-phenyl)-3-methyl-butan-1-one (19.1 g, 38.9 mmol) in dimethyl sulfide (146 mL) at room temperature under argon gas. Heat the reaction mixture gently to reflux overnight. Quench the reaction mixture with ice-water and stir for 1 hr. Separate the organic layer and extract the aqueous with ethyl acetate (3×). Combine the organic layers, wash with brine, dry over sodium sulfate, and concentrate to give a crude oil. Purify the resulting crude oil by flash column chromatography (silica gel) eluting with 25% ethyl acetate/hexane to provide the title compound as a tan solid (5.3 g, 20.2 mmol, 52% yield). MS (m/z): 263 (M+1).

Workup

  1. temperatureHeat the reaction mixture gently
  2. temperatureto reflux overnight
  3. customQuench the reaction mixture with ice-water
  4. customSeparate the organic layer
  5. extractionextract the aqueous with ethyl acetate (3×)
  6. washCombine the organic layers, wash with brine
  7. dry with materialdry over sodium sulfate
  8. concentrationconcentrate
  9. customto give a crude oil
  10. customPurify the resulting crude oil by flash column chromatography (silica gel)
  11. washeluting with 25% ethyl acetate/hexane

Sources & evidence

ORD record
ord-963ab6fdca48410d974e47387fa5d9c1
Source dataset
uspto-grants-2010_07
Patent number
US07754742B2

Reaction notes

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