Tetrahydrofuran → HCID 178447715, compound

HRID 863727Notes

Reaction equation

HRID 863727 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.[CH2:41]([Si:46]1([C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)[CH2:51][CH2:50][CH:49]([CH:52]2[CH2:57][CH2:56][CH:55]([CH:58]=O)[CH2:54][CH2:53]2)[CH2:48][CH2:47]1)[CH2:42][CH2:43][CH2:44][CH3:45]>CCCCCC.O>[F:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:58][C@H:55]2[CH2:54][CH2:53][C@H:52]([CH:49]3[CH2:48][CH2:47][Si:46]([CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])([C:60]4[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=4)[CH2:51][CH2:50]3)[CH2:57][CH2:56]2)[CH:32]=[CH:33][C:34]=1[F:35]

Participants

7

Reactant 4

HCID 8028Tetrahydrofuran3×HCID 107904853,4-Difluorobenzyltriphenylphosphonium bromideHCID 23665647Potassium tert-butoxideHCID 538633044-(4-Phenyl-4-n-pentyl-4-silacyclohexyl)cyclohexane carbaldehyde

Product 1

HCID 178447715HCID 178447715, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

12.0 g of potassium t-butoxide was added to a mixture of 47.0 g of 3,4-difluorobenzyltriphenylphosphonium bromide and 200 ml of tetrahydrofuran (hereinafter referred to as THF) to obtain an orange-colored ylide solution. 50 ml of a THF solution of 35.0 g of 4-(4-n-pentyl-4-phenyl-4-silacyclohexyl)cyclohexane carbaldehyde was added to the solution, followed by agitation at room temperature for 2 hours. Thereafter, the reaction solution was poured into iced water and extracted with ethyl acetate. The resultant extract was washed with brine, dried and concentrated to obtain a residue, to which 100 ml of n-hexane was added. The resultant crystals of triphenylphosphine oxide were separated by filtration and the resultant filtrate was concentrated. The resultant residue was purified through silica gel chromatography to obtain 41.7 g of 4-(trans-4-(2-(3,4-difluorophenyl)ethenyl)cyclohexyl)-1-n-pentyl-1-phenyl-1-silacyclohexane. This product was subjected to IR analysis with the results shown below.

Workup

  1. customto obtain an orange-colored ylide solution
  2. extractionextracted with ethyl acetate
  3. extractionThe resultant extract
  4. washwas washed with brine
  5. customdried
  6. concentrationconcentrated
  7. customto obtain a residue
  8. customThe resultant crystals of triphenylphosphine oxide were separated by filtration
  9. concentrationthe resultant filtrate was concentrated
  10. customThe resultant residue was purified through silica gel chromatography

Sources & evidence

ORD record
ord-07a941a7930e4f90b59e1ec72519987e
Source dataset
uspto-grants-1996_10
Patent number
US05560866

Reaction notes

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