Sodium Hydroxide → 4-Methyl-1-(triphenyl-lambda5-phosphanylidene)-pentan-2-one

HRID 1377429Notes

Reaction equation

HRID 1377429 reaction equation
[Br-].[CH2:2]([C:6]([CH2:8][P+:9]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])[CH:3]([CH3:5])[CH3:4].[OH-].[Na+]>C(Cl)Cl>[CH2:2]([C:6]([CH:8]=[P:9]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])[CH:3]([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22914202Isobutylcarbonylmethyltriphenylphosphonium bromide

Product 1

HCID 150165704-Methyl-1-(triphenyl-lambda5-phosphanylidene)-pentan-2-oneYield 79.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

111.6 g of isobutylcarbonylmethyltriphenylphosphonium bromide in 1500 ml of methylene chloride is mixed with 1500 ml of 2N NaOH and stirred for 30 minutes at room temperature. The organic phase is separated, washed with water and dried on sodium sulfate. After filtration and evaporation of the solvent, the residue is recrystallized in tert-butyl methyl ether. 72.2 g of title compound 1, with a melting point of 120°-121° C., is obtained. By variations of the ketone component in reaction step a), other phosphoranes of the formula can be produced analogously. ##STR9## II. (5E,7E,22E)-(1S,3R)-1,3-bis-(tert-butyl-dimethyl silyloxy-9,10-seco-24a-homo-5,7,10(19)-22-cholestatetraene-24-one 2

Workup

  1. customThe organic phase is separated
  2. washwashed with water
  3. customdried on sodium sulfate
  4. filtrationAfter filtration and evaporation of the solvent
  5. customthe residue is recrystallized in tert-butyl methyl ether

Sources & evidence

ORD record
ord-f7ca1c1f2c2448ceb9f1209662dbb69b
Source dataset
uspto-grants-1997_09
Patent number
US05665716

Reaction notes

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