HCID 86759660, compound → HCID 20775664, compound

HRID 1815990Notes

Reaction equation

HRID 1815990 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9]/[C:10](/[C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:5][CH:4]=1>CCO.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH:10]([C:17]2[CH:18]=[CH:19][C:20]([C:23]([F:24])([F:26])[F:25])=[CH:21][CH:22]=2)[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 86759660HCID 86759660, compound

Product 1

HCID 20775664HCID 20775664, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a suspension of 10% Pd/C (600 mg) in absolute EtOH (50 mL) was added ethyl (±)-4-(4-methoxyphenyl)-3-[4(trifluoromethyl)phenyl]crotonate (2.2 g. 6 mmole), and the mixture was shaken on a Parr apparatus at RT under H2 (50 psi). After 4 hr, the mixture was filtered through a pad of celite®, and the filtrate was concentrated. This reaction sequence was repeated three times. The residue was chromatographed on silica gel (35% EtOAc/hexanes) to afford the title compound (900 mg, 56%) as an oil: TLC (5% EtOAc/hexanes) Rf0.46; 1H NMR (300 MHz, CDCl3) δ 7.51 (d, J=8.2 Hz, 2 H), 7.24 (d, J=8.2 Hz, 2 H), 6.94 (d, J=8.7 Hz, 2 H), 6.76 (d, J=8.7 Hz, 2 H), 3.99 (q, J=7.1 Hz, 2 H), 3.76 (s, 3H), 3.35-3.50 (m, 1 H), 2.75-2.93 (m, 2H), 2.69 (dd, J=15.6, 6.4 Hz, 1 H), 2.60 (dd, J=15.6, 8.9 Hz, 1H), 1.11 (t, J=7.1 Hz 3 H).

Workup

  1. filtrationthe mixture was filtered through a pad of celite®
  2. concentrationthe filtrate was concentrated
  3. customThe residue was chromatographed on silica gel (35% EtOAc/hexanes)

Sources & evidence

ORD record
ord-6f8e6de4d60c4247856d0a6387fe61fe
Source dataset
uspto-grants-2005_04
Patent number
US06881736B1

Reaction notes

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