HCID 68983819, compound → HCID 68981345, compound

HRID 2217801Notes

Reaction equation

HRID 2217801 reaction equation
[F:1][C:2]([F:16])([F:15])[CH:3]1[CH2:8][CH2:7][C:6](=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:5][CH2:4]1.[H][H]>C(OCC)(=O)C.[Pd]>[F:1][C:2]([F:15])([F:16])[CH:3]1[CH2:4][CH2:5][CH:6]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:7][CH2:8]1

Participants

5

Reactant 2

HCID 68983819HCID 68983819, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68981345HCID 68981345, compoundYield 79.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of [4-(trifluoromethyl)cyclohexylidene]-acetic acid, ethyl ester (Example 8 (a)) (1 g) in ethyl acetate (20 mL) was added 5% palladium on carbon (450 mg). The mixture was stirred at room temperature under a 2 bar atmosphere of hydrogen. The reaction mixture was then filtered through diatomaceous earth and concentrated. Purification (SiO2, ethyl acetate:isohexane 1:19 as eluant) gave 4-(trifluoromethyl)-cyclohexaneacetic acid, ethyl ester (800 mg), which was dissolved in methanol (3 mL). Potassium hydroxide (1 g) in water (3 mL) was added and the mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated and subsequently acidified to pH1 with aqueous 2M hydrochloric acid. The resulting solution was extracted with dichloromethane (3×10 mL) and the combined organic extracts dried, filtered and evaporated to give the sub-title compound as an oil (660 mg).

Workup

  1. filtrationThe reaction mixture was then filtered through diatomaceous earth
  2. concentrationconcentrated
  3. customPurification (SiO2, ethyl acetate:isohexane 1:19 as eluant)

Sources & evidence

ORD record
ord-dcfaa4d0f7ae48c79e66c8415663ad69
Source dataset
uspto-grants-2008_08
Patent number
US07408065B2

Reaction notes

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