[(4-Ethoxyphenyl)methyl](triphenyl)phosphanium bromide → HCID 53785709, compound

HRID 260237Notes

Reaction equation

HRID 260237 reaction equation
C([Li])CCC.[Br-].[CH2:7]([O:9][C:10]1[CH:35]=[CH:34][C:13]([CH2:14][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:12][CH:11]=1)[CH3:8].[CH2:36]([Si:41]1([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[CH2:46][CH2:45][CH:44]([CH:47]=O)[CH2:43][CH2:42]1)[CH2:37][CH2:38][CH2:39][CH3:40]>CCCCCC.O.O1CCCC1>[CH2:7]([O:9][C:10]1[CH:11]=[CH:12][C:13]([CH:14]=[CH:47][CH:44]2[CH2:43][CH2:42][Si:41]([CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[CH2:46][CH2:45]2)=[CH:34][CH:35]=1)[CH3:8]

Participants

7

Reactant 3

HCID 2724470[(4-Ethoxyphenyl)methyl](triphenyl)phosphanium bromideHCID 15300717HCID 15300717, compoundHCID 178418339Butyllithium

Product 1

HCID 53785709HCID 53785709, compoundYield 97%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent2×

Procedure

65 ml of an n-hexane solution of 1.60 moles of n-butyl lithium was added to a mixture of 48.0 g of p-ethoxybenzyltriphenylphosphonium bromide and 200 ml of tetrahydrofuran to obtain a ylide solution. 27.4 g of 4-n-pentyl-4-phenyl-4-silacyclohexane carbaldehyde was dropped in the solution. After agitation at room temperature for 2 hours, the resultant solution was charged into iced water and extracted with ethyl acetate. The extract was subjected to ordinary washing and concentrating operations 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 silica gel column chromatography to obtain 38.0 g (yield: 97%) of 4-(2-(4-ethoxyphenyl)ethenyl)-1-n-pentyl-1-phenyl-1-silacyclohexane.

Workup

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

Sources & evidence

ORD record
ord-239f4a0ad80c468182eae33d78cc2286
Source dataset
uspto-grants-1996_06
Patent number
US05527490

Reaction notes

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