HCID 68326436, compound → HCID 68326349, compound

HRID 2359007Notes

Reaction equation

HRID 2359007 reaction equation
[CH2:1]([O:3][C:4](=[O:31])/[C:5](/[C:17]([CH:19]1[CH2:24][CH2:23][CH:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:21][CH2:20]1)=[O:18])=[CH:6]\[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=1)[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:31])[CH:5]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:15])([F:16])[F:14])[CH:8]=1)[C:17](=[O:18])[CH:19]1[CH2:24][CH2:23][CH:22]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:21][CH2:20]1)[CH3:2]

Participants

4

Reactant 1

HCID 68326436HCID 68326436, compound

Product 1

HCID 68326349HCID 68326349, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of (Z)-2-(4-phenylcyclohexanecarbonyl)-3-(3-trifluoromethylphenyl)-acrylic acid ethyl ester (10) (12.3 g, 28.6 mmol) and 10% Pd on carbon (2.5 g, 20% by weight) in denatured ethanol (250 mL) was stirred under a hydrogen atmosphere for 2 hr. The solids were removed by filtration through celite and washed with ethanol. The filtrate was evaporated under vacuum to yield a clear oil. The residue was purified by column chromatography on silica gel (gradient: 0 to 10% tert-butyl methyl ether in cyclohexane) to afford 8.6 g (70%) of 3-oxo-3-(4-phenylcyclohexyl)-2-(3-trifluoromethylbenzyl)-propionic acid ethyl ester (22). 1H NMR (400 MHz, 192227). LCMS (method A), Rt=4.76 min, (M+H)+=433.2 (94%); Rt=5.22 min, (M+H)+=262.9 (6.5%).

Workup

  1. customThe solids were removed by filtration through celite
  2. washwashed with ethanol
  3. customThe filtrate was evaporated under vacuum
  4. customto yield a clear oil
  5. customThe residue was purified by column chromatography on silica gel (gradient: 0 to 10% tert-butyl methyl ether in cyclohexane)

Sources & evidence

ORD record
ord-42390f9bde0a4219991b48af0c8a68a6
Source dataset
uspto-grants-2014_04
Patent number
US08685973B2

Reaction notes

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