Water → HCID 54188169, compound

HRID 1769578Notes

Reaction equation

HRID 1769578 reaction equation
[Br-].[F:2][C:3]1[CH:4]=[C:5]([CH:26]=[C:27]([F:30])[C:28]=1[F:29])[CH2:6][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C[O-].[Na+].[CH:34]([CH:36]1[CH2:41][CH2:40][C:39](=[O:42])[CH2:38][CH2:37]1)=O.O>C1COCC1>[F:30][C:27]1[CH:26]=[C:5]([CH:6]=[CH:34][CH:36]2[CH2:41][CH2:40][C:39](=[O:42])[CH2:38][CH2:37]2)[CH:4]=[C:3]([F:2])[C:28]=1[F:29]

Participants

6

Reactant 4

HCID 962WaterHCID 10942334Sodium MethoxideHCID 111709734-Oxocyclohexane-1-carbaldehydeHCID 22385338HCID 22385338, compound

Product 1

HCID 54188169HCID 54188169, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 3,4,5-trifluorobenzyltriphenylphosphonium bromide (234 g) in THF (500 ml) was stirred in a nitrogen gas stream, followed by adding sodium methoxide (32.4 g) little by little at room temperature, stirring the reaction solution at room temperature for one hour, dropwise adding a solution of 4-formylcyclohexanone (50 g) in THF (250 ml), stirring the mixture at room temperature for 2 hours, adding it to water (1 l) extracting with ethyl acetate (1 1), washing the organic layer with water, drying over anhydrous MgSO4, concentrating the solvent under reduced pressure, to obtain 4-(2'-(3",4",5"-trifluorophenyl)ethenyl)cyclohexanone (71 g).

Workup

  1. stirringstirring the reaction solution at room temperature for one hour
  2. stirringstirring the mixture at room temperature for 2 hours
  3. extractionextracting with ethyl acetate (1 1)
  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-d5240498d3474814850bf80115b42836
Source dataset
uspto-grants-1995_01
Patent number
US05382379

Reaction notes

Loading…