Benzyl 3-fluoro-2-(fluoromethyl)-2-methylpropanoate → 3-Fluoro-2-(fluoromethyl)-2-methylpropanoic acid
Reaction equation
[F:1][CH2:2][C:3]([CH2:15][F:16])([CH3:14])[C:4]([O:6]CC1C=CC=CC=1)=[O:5]>CCOC(C)=O.[Pd]>[F:1][CH2:2][C:3]([CH2:15][F:16])([CH3:14])[C:4]([OH:6])=[O:5]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a stirred solution of Intermediate 209A (0.300 g, 1.314 mmol) in EtOAc (5 mL) was added 10% Pd/C (0.140 g, 0.131 mmol). The reaction mixture was stirred for 12 h under an atmosphere of hydrogen (15 psi). The reaction mixture was then filtered through a pad of CELITE® and the cake was washed with EtOAc. The filtrate was concentrated under reduced pressure to afford Intermediate 209B as a yellow liquid (160 mg, 88%). The crude product was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 13.02 (bs, 1H), 4.40-4.66 (m, 4H), 1.06-1.20 (m, 3H).
Workup
- filtrationThe reaction mixture was then filtered through a pad of CELITE®
- washthe cake was washed with EtOAc
- concentrationThe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-2358fd7b239647bbbdf4a346b3ba8091
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09273058B2
Reaction notes
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