Ethyl 4-(3-chloro-4-fluorophenyl)cyclohex-3-ene-1-carboxylate → HCID 178472336, compound

HRID 604665Notes

Reaction equation

HRID 604665 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH2:14][CH2:13][CH:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[F:8]>CCOC(C)=O.[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[CH2:10][CH2:11][C@H:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:13][CH2:14]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 1

HCID 67057759Ethyl 4-(3-chloro-4-fluorophenyl)cyclohex-3-ene-1-carboxylate

Product 1

HCID 178472336HCID 178472336, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 4-(3-chloro-4-fluorophenyl)cyclohex-3-ene-1-carboxylate (270 mg, 0.955-mmoL) in EtOAc (15 mL) was added 10% Pd/C (45 mg). The reaction was put under an atmosphere of H2 (balloon) and stirred vigorously at room temperature. After 30 min, the catalyst was removed by filtration, and the filtrate was concentrated to afford a mixture of cis and trans products. The desired trans isomer was separated by flash chromatography on silica gel (0 to 10% EtOAc/hexanes) to afford ethyl trans-4-(3-chloro-4-fluorophenyl)cyclohexanecarboxylate. Rf=0.25 (5% EtOAc/hexanes). 1H NMR (500 MHz, CDCl3): δ 7.21 (d, J=7.3 Hz, 1H), 7.02-7.06 (m, 2H), 4-14 (q, J=7.1 Hz, 2H), 2.48 (m, 1H), 2.32 (m, 1H), 2.08-2.12 (m, 2H), 1.91-1.98 (m, 2H), 1.53-1.67 (m, 2H), 1.37-1.46 (m, 2H), 1.27 (t, J=7.1 Hz, 3H).

Workup

  1. customthe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customto afford
  4. additiona mixture of cis and trans products
  5. customThe desired trans isomer was separated by flash chromatography on silica gel (0 to 10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-7623c83a420a4f80a1d1061b4b24a641
Source dataset
uspto-grants-2011_03
Patent number
US07910592B2

Reaction notes

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