Ethanol → 4-(2-Fluorophenyl)oxane-4-carboxylic acid
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([C:14]([O:16]C)=[O:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.CCO.[OH-].[K+]>O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([C:14]([OH:16])=[O:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 130 °C
Procedure
A solution of methyl 4-(2-fluorophenyl)-tetrahydro-2H-pyran-4-carboxylate (2.45 g, 10 mmol), water (10 mL, 555 mmol), EtOH (50 mL, 10 mmol) and KOH (2.3 g, 41 mmol) was placed in a sealed flask and then heated at 130° C. for 10 hours. After cooling to room temperature, the reaction was concentrated to afford a yellow oil. The residue was diluted with water (100 mL) and extracted with DCM (120 mL). The separated aqueous phase was then acidified to pH=1 and then extracted with EtOAc (3×10 mL). The organic later was dried (Na2SO4), filtered, and concentrated to afford a tan solid (1.9 g). MS m/e=223.1 (M−1)−.
Workup
- temperatureAfter cooling to room temperature
- concentrationthe reaction was concentrated
- customto afford a yellow oil
- extractionextracted with DCM (120 mL)
- extractionextracted with EtOAc (3×10 mL)
- dry with materialThe organic later was dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-0d9dc3cb17cb489abdec07e90be1de97
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07635715B2
Reaction notes
Loading…