HCID 58597415, compound → HCID 68536721, compound

HRID 1992943Notes

Reaction equation

HRID 1992943 reaction equation
[F:1][C:2]([F:18])([F:17])/[C:3](/[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[CH:4]/[C:5]([O:7][CH2:8][CH3:9])=[O:6]>[Pd]>[F:1][C:2]([F:17])([F:18])[CH:3]([CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

3

Reactant 1

HCID 58597415HCID 58597415, compound

Product 1

HCID 68536721HCID 68536721, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Ethyl (2E)-4,4,4-trifluoro-3-(phenylmethyl)-2-butenoate (175-E) (0.85 g, 3.30 mmol) was hydrogenated at room temperature with 10% Pd/C under a hydrogen balloon to yield 0.77 g (90%) of the title compound (176) as a colorless oil. From ethyl (2Z)-4,4,4-trifluoro-3-(phenylmethyl)-2-butenoate (175-Z) (0.35 g, 1.36 mmol), 0.31 g (88%) of the title compound (176) was obtained as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 1.18 (t, J=7.2 Hz, 3H), 2.35 (dd, J1=16.4 Hz, J2=6.3 Hz, 1H), 2.55 (dd, J1=16.5 Hz, J2=6.2 Hz, 1H), 2.60-2.70 (m, 1H), 3.00-3.15 (m, 2H), 4.00 (q, J=7.2 Hz, 2H), 7.15-7.25 (m, 3H), 7.26-7.35 (m, 2H).

Sources & evidence

ORD record
ord-8ea11ec56aea424cb78453dc7be2bc37
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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