Tetrahydrofuran → 4-(4-(2-(3,4-Difluorophenyl)ethenyl)cyclohexyl)-1-phenyl-1-n-propyl-1-silacyclohexane

HRID 440609Notes

Reaction equation

HRID 440609 reaction equation
CC(C)([O-])C.[K+].[Br-].[F:8][C:9]1[CH:10]=[C:11]([CH:32]=[CH:33][C:34]=1[F:35])[CH2:12][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1.[C:41]1([Si:47]2([CH2:61][CH2:62][CH3:63])[CH2:52][CH2:51][CH:50]([CH:53]3[CH2:58][CH2:57][CH:56]([CH:59]=O)[CH2:55][CH2:54]3)[CH2:49][CH2:48]2)[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>CCCCCC.O>[F:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:59][CH:56]2[CH2:57][CH2:58][CH:53]([CH:50]3[CH2:49][CH2:48][Si:47]([C:41]4[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=4)([CH2:61][CH2:62][CH3:63])[CH2:52][CH2:51]3)[CH2:54][CH2:55]2)[CH:32]=[CH:33][C:34]=1[F:35]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 107904853,4-Difluorobenzyltriphenylphosphonium bromideHCID 23665647Potassium tert-butoxideHCID 536682054-(4-Phenyl-4-n-propyl-4-silacyclohexyl)cyclohexane carbaldehyde

Product 1

HCID 537852304-(4-(2-(3,4-Difluorophenyl)ethenyl)cyclohexyl)-1-phenyl-1-n-propyl-1-silacyclohexaneYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

12.0 g of potassium t-butoxide was added to a mixture of 48.0 g of 3,4-difiuorobenzyltriphenylphosphonium bromide and 400 ml of tetrahydrofuran to obtain a ylide solution. 32.9 g of 4-(4-phenyl-4-n-propyl-4-silacyclohexyl)cyclohexane carbaldehyde was dropped in the solution. After agitation at room temperature for 2 hours, the reaction mixture was charged into water and extracted with ethyl acetate. The ethyl acetate phase or solution was subjected to washing with brine, drying and concentration to obtain a residue, to which n-hexane was added. The resultant crystals of triphenylphosphine oxide were removed by filtration and the flitrate was concentrated. The resultant residue was purified through column chromatography to obtain 39.9 g (yield: 91%) of 4-(4-(2-(3,4-difluorophenyl)ethenyl)cyclohexyl)-1-phenyl-1-n-propyl-1-silacyclohexane.

Workup

  1. customto obtain a ylide solution
  2. extractionextracted with ethyl acetate
  3. washto washing with brine
  4. customdrying
  5. concentrationconcentration
  6. customto obtain a residue
  7. customThe resultant crystals of triphenylphosphine oxide were removed by filtration
  8. concentrationthe flitrate was concentrated
  9. customThe resultant residue was purified through column chromatography

Sources & evidence

ORD record
ord-1ff61405f7944304bbbbfb0c5bd5141e
Source dataset
uspto-grants-1996_05
Patent number
US05519156

Reaction notes

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