(R)-Methyl 4-(4-fluoro-3-methylphenyl)-4-hydroxybutanoate → (R)-5-(4-fluoro-3-methyl-phenyl)-dihydro-furan-2-one

HRID 1643279Notes

Reaction equation

HRID 1643279 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([OH:15])[CH2:9][CH2:10][C:11](OC)=[O:12])=[CH:4][C:3]=1[CH3:16]>C(Cl)Cl.C(O)(C(F)(F)F)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[O:15][C:11](=[O:12])[CH2:10][CH2:9]2)=[CH:4][C:3]=1[CH3:16]

Participants

4

Reactant 1

HCID 59568813(R)-Methyl 4-(4-fluoro-3-methylphenyl)-4-hydroxybutanoate

Product 1

HCID 59568816(R)-5-(4-fluoro-3-methyl-phenyl)-dihydro-furan-2-oneYield 112.5%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of (R)-methyl 4-(4-fluoro-3-methyl-phenyl)-4-hydroxy-butanoate (289 mg) in 20 mL DCM was added 4 drops TFA at room temperature and the resulting solution warmed to 40° C. After stirring for 16 h the reaction was cooled to room temperature and concentrated under reduced pressure. The product was isolated by flash column chromatograph eluting with 0% to 30% ethyl acetate/hexane gradient solvent to give 279 mg of (R)-5-(4-fluoro-3-methyl-phenyl)-dihydro-furan-2-one as a colorless oil.

Workup

  1. temperaturewas cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customThe product was isolated by flash column chromatograph
  4. washeluting with 0% to 30% ethyl acetate/hexane gradient solvent

Sources & evidence

ORD record
ord-1e875457ca2742e7b734a21284f009f4
Source dataset
uspto-grants-2012_02
Patent number
US08119692B2

Reaction notes

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