methyl (2E)-3-(3',5'-difluorobiphenyl-4-yl)prop-2-enoate → Methyl 3-(3',5'-difluorobiphenyl-4-yl)propanoate

HRID 2410458Notes

Reaction equation

HRID 2410458 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[C:17]([O:19][CH3:20])=[O:18])=[CH:11][CH:10]=2)[CH:5]=[C:6]([F:8])[CH:7]=1>C(OCC)(=O)C.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:13][CH:14]=2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 1

HCID 67182516methyl (2E)-3-(3',5'-difluorobiphenyl-4-yl)prop-2-enoate

Product 1

HCID 67181936Methyl 3-(3',5'-difluorobiphenyl-4-yl)propanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the compound obtained from step b above (0.79 g) in a mixture of ethyl acetate (˜10 mL), 10% Palladium on charcoal (0.2 g) was added and stirred under hydrogen atmosphere at 30 psi for 2.5 hours. The reaction mixture was filtered through a celite pad washed with ethyl acetate and the filtrate was concentrated under reduced pressure to obtain the title compound (0.77 g) as white solid which was used as such for the next step.

Workup

  1. additionwas added
  2. filtrationThe reaction mixture was filtered through a celite pad
  3. washwashed with ethyl acetate
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-946180417dd147f3b2044c4a37ad20bd
Source dataset
uspto-grants-2014_08
Patent number
US08816073B2

Reaction notes

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