Water → Ethyl cyclohexylideneacetate

HRID 1769582Notes

Reaction equation

HRID 1769582 reaction equation
[CH3:1][C:2](C)([O-:4])C.[K+].FC1C=[C:10]([CH:16]2[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]2)[CH:11]=C(F)C=1F.[OH2:23]>C1COCC1>[CH2:2]([O:4][C:11]([CH:10]=[C:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1)=[O:23])[CH3:1]

Participants

5

Reactant 3

HCID 962WaterHCID 219932844-(3,4,5-Trifluorophenyl)cyclohexan-1-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 73776Ethyl cyclohexylideneacetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of triethyl phosphonoacetate (21.8 g) in THF (50 ml) was stirred in a nitrogen gas stream, followed by adding potassium-t-butoxide (11.8 g) little by little at room temperature, stirring the reaction solution at room temperature for one hour, dropwise adding a solution of 4-(3',4',5'-trifluorophenyl)cyclohexanone (20 g) in THF (50 ml), stirring at room temperature for 2 hours, adding to water (100 ml), extracting with ethyl acetate (100 ml), washing the organic layer with water, drying over anhydrous MgSO4 and concentrating the solvent under reduced pressure, to obtain 4-(3',4',5'-trifluorophenyl))ethoxycarbonylmethylenecyclohexane (18.3 g).

Workup

  1. stirringstirring the reaction solution at room temperature for one hour
  2. stirringstirring at room temperature for 2 hours
  3. extractionextracting with ethyl acetate (100 ml)
  4. washwashing the organic layer with water
  5. dry with materialdrying over anhydrous MgSO4
  6. concentrationconcentrating the solvent under reduced pressure

Sources & evidence

ORD record
ord-06f97a4fe8a04746bd885910931cd362
Source dataset
uspto-grants-1995_01
Patent number
US05382379

Reaction notes

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