Water → HCID 67328702, compound

HRID 1841832Notes

Reaction equation

HRID 1841832 reaction equation
[F:1]/[C:2](/[Si](CC)(CC)CC)=[C:3](/[F:13])\[CH:4]1[CH2:9][CH2:8][CH:7]([CH2:10][CH2:11][CH3:12])[CH2:6][CH2:5]1.O.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CC(OC)(C)C>[F:13]/[C:3](/[CH:4]1[CH2:9][CH2:8][CH:7]([CH2:10][CH2:11][CH3:12])[CH2:6][CH2:5]1)=[CH:2]/[F:1]

Participants

6

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 71074322[(Z)-1,2-difluoro-2-(4-propylcyclohexyl)vinyl]triethylsilane

Product 1

HCID 67328702HCID 67328702, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

34.6 g (0.11 mol) of [(Z)-1,2-difluoro-2-(4-propylcyclohexyl)vinyl]triethylsilane are refluxed for 20 h in 900 ml of THF together with 45 ml of water and 160 ml of TBAF (0.16 mol, 1 M soln. in THF). The batch is diluted with MTBE and washed a number of times with water. The aqueous phases are extracted with MTBE, and the combined organic phases are washed with water and saturated sodium chloride solution. The solution is dried using sodium sulfate and concentrated under reduced pressure. The residue is purified by column chromatography (SiO2, pentane), giving 1-((E)-1,2-difluorovinyl)-4-propylcyclohexane as a colourless oil.

Workup

  1. washwashed a number of times with water
  2. extractionThe aqueous phases are extracted with MTBE
  3. washthe combined organic phases are washed with water and saturated sodium chloride solution
  4. customThe solution is dried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by column chromatography (SiO2, pentane)

Sources & evidence

ORD record
ord-7de38795d58d4a14acea9041ea0f462f
Source dataset
uspto-grants-2015_02
Patent number
US08945420B2

Reaction notes

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