Methanol → HCID 58254749, compound

HRID 1643277Notes

Reaction equation

HRID 1643277 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:14])[CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:4][C:3]=1[CH3:15].OS(O)(=O)=O.[CH3:21]O>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:14])[CH2:9][CH2:10][C:11]([O:13][CH3:21])=[O:12])=[CH:4][C:3]=1[CH3:15]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 64854434-(4-Fluoro-3-methylphenyl)-4-oxobutanoic acid

Product 1

HCID 58254749HCID 58254749, compound

Procedure

To a solution of 4-(4-fluoro-3-methylphenyl)-4-oxobutanoic acid in 30 mL methanol was added concentrated H2SO4 (300 mL) at room temperature and the resulting mixture was stirred for 16 h. The mixture was concentrated under reduced pressure and the residue treated with 30 mL water and the resulting mixture extracted with ethyl acetate (3×40 mL). The combined organic layers were washed with brine (2×20 mL) and dried over Na2SO4. The product was isolated by flash column chromatography eluting with 0% to 10% ethyl acetate/hexane gradient solvent to give 568 mg of the title compound as a colorless oil.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionthe residue treated with 30 mL water
  3. extractionthe resulting mixture extracted with ethyl acetate (3×40 mL)
  4. washThe combined organic layers were washed with brine (2×20 mL)
  5. dry with materialdried over Na2SO4
  6. customThe product was isolated by flash column chromatography
  7. washeluting with 0% to 10% ethyl acetate/hexane gradient solvent

Sources & evidence

ORD record
ord-68ed18f326334238b8fd2fb1b2f3e995
Source dataset
uspto-grants-2012_02
Patent number
US08119692B2

Reaction notes

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