Water → 4-(4-Phenyl-4-n-pentyl-4-silacyclohexyl)cyclohexane carbaldehyde

HRID 2658Notes

Reaction equation

HRID 2658 reaction equation
C[C:2](C)([O-:4])C.[K+].[Cl-].COC[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH2:30]([Si:35]1([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[CH2:40][CH2:39][CH:38]([CH:41]2[CH2:46][CH2:45][C:44](=O)[CH2:43][CH2:42]2)[CH2:37][CH2:36]1)[CH2:31][CH2:32][CH2:33][CH3:34].O>C1COCC1>[CH2:30]([Si:35]1([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[CH2:36][CH2:37][CH:38]([CH:41]2[CH2:46][CH2:45][CH:44]([CH:2]=[O:4])[CH2:43][CH2:42]2)[CH2:39][CH2:40]1)[CH2:31][CH2:32][CH2:33][CH3:34]

Participants

6

Reactant 4

HCID 962WaterHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 110678544-(4-n-Pentyl-4-phenyl-4-silacyclohexyl)cyclohexanoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 538633044-(4-Phenyl-4-n-pentyl-4-silacyclohexyl)cyclohexane carbaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

12 g of potassium t-butoxide was added to a mixture of 35 g of methoxymethyltriphenylphosphonium chloride and 200 ml of THF to prepare an orange ylide solution. A solution of 34 g of 4-(4-n-pentyl-4-phenyl-4-silacyclohexyl)cyclohexanone in 50 ml of THF was added to the ylide solution and agitated at room temperature for 2 hours. Thereafter, the mixture was poured into iced water and extracted with methylene chloride, followed by washing, drying and concentration by a usual manner. n-Hexane was added to the residue, and the resultant crystals of triphenylphosphine oxide were removed by filtration. The filtrate was concentrated, and the resultant residue was hydrolyzed with 100 ml of 20% hydrochloric acid, followed by washing, drying and concentration by a usual manner to obtain 4-(4-n-pentyl-4-phenyl-4-silacyclohexyl)cyclohexane carbaldehyde.

Workup

  1. customto prepare an orange ylide solution
  2. extractionextracted with methylene chloride
  3. washby washing
  4. customdrying
  5. concentrationconcentration by a usual manner
  6. additionn-Hexane was added to the residue
  7. customthe resultant crystals of triphenylphosphine oxide were removed by filtration
  8. concentrationThe filtrate was concentrated
  9. washby washing
  10. customdrying
  11. concentrationconcentration by a usual manner

Sources & evidence

ORD record
ord-60ff9b3f88b74fb89fc2c3b2f2e968f6
Source dataset
uspto-grants-1998_03
Patent number
US05730901

Reaction notes

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