Acetic Acid → HCID 68326436, compound

HRID 631844Notes

Reaction equation

HRID 631844 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][C:6](=[O:19])[CH:7]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:9][CH2:8]1)[CH3:2].[F:21][C:22]([F:32])([F:31])[C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH:26]=O.C(O)(=O)C>C1(C)C=CC=CC=1.C(OCC)(=O)C.N1CCCCC1>[CH2:1]([O:3][C:4](=[O:20])/[C:5](/[C:6]([CH:7]1[CH2:8][CH2:9][CH:10]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:11][CH2:12]1)=[O:19])=[CH:26]\[C:25]1[CH:28]=[CH:29][CH:30]=[C:23]([C:22]([F:21])([F:31])[F:32])[CH:24]=1)[CH3:2]

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 679903-(Trifluoromethyl)benzaldehydeHCID 68326348HCID 68326348, compound

Product 1

HCID 68326436HCID 68326436, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 8082PiperidineCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Oxo-3-(4-phenyl-cyclohexyl)-propionic acid ethyl ester (7) (11.56 g, 42.1 mmol), 3-trifluoromethylbenzaldehyde (11 g, 63.15 mmol), glacial acetic acid (7.16 mmol, 0.41 mL) and piperidine (2.1 mmol, 0.21 mL) were dissolved in toluene (250 mL) and heated under Dean and Stark conditions at reflux for 48 hours. The cooled reaction mixture was diluted with an equal volume of ethyl acetate and washed with 1M aq. HCl and brine. The organics were dried over sodium sulfate, filtered, and evaporated to afford a clear, brown oil. The residue was purified by column chromatography on silica gel (gradient: 0 to 10% tert-butyl methyl ether in cyclohexane) to afford 12.3 g (68%) of (Z)-2-(4-phenylcyclohexanecarbonyl)-3-(3-trifluoromethyl-phenyl)-acrylic acid ethyl ester. 1H NMR (400 MHz, 192191), LCMS (method C), Rt=4.77 min, (M+H)+=431.2.

Workup

  1. temperatureheated under Dean and Stark conditions
  2. temperatureat reflux for 48 hours
  3. customThe cooled reaction mixture
  4. washwashed with 1M aq. HCl and brine
  5. dry with materialThe organics were dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto afford a clear, brown oil
  9. 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-9d0fac2773d54540a8924a9b7349d92f
Source dataset
uspto-grants-2016_04
Patent number
US09321736B2

Reaction notes

Loading…