(R)-Methyl 4-(4-fluorophenyl)-4-hydroxybutanoate → (R)-5-(4-fluorophenyl)dihydrofuran-2(3H)-one
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([OH:15])[CH2:9][CH2:10][C:11]([O:13]C)=O)=[CH:4][CH:3]=1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]2[O:15][C:11](=[O:13])[CH2:10][CH2:9]2)=[CH:6][CH:7]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 40 °C
Procedure
To a solution of (R)-methyl 4-(4-fluorophenyl)-4-hydroxybutanoate (1.7 g, 8.0 mmol) in DCM (40 mL) was added 8 drops TFA at room temperature. The reaction mixture was warmed to 40° C. and stirred for 16 h. Evaporation of the solvent gave a light yellow oil from which the product was isolated by Flash chromatography eluting with 0% to 30% ethyl acetate/hexane to give 1.6 g of the title compound as a colorless oil.
Workup
- customEvaporation of the solvent
- customgave a light yellow oil from which the product
- customwas isolated by Flash chromatography
- washeluting with 0% to 30% ethyl acetate/hexane
Sources & evidence
- ORD record
- ord-9487e399c11e450f8fedc53eceec88ba
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08119692B2
Reaction notes
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