Water → HCID 57125215, compound

HRID 1649349Notes

Reaction equation

HRID 1649349 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)[CH2:19][C:20](=[O:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].O>O1CCCC1.C(OCC)C>[C:1]1([CH2:7][CH2:8][CH:9]=[CH:19][C:20](=[O:26])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 31234BenzenepropanolHCID 20479549(2-Oxoheptyl)(triphenyl)phosphanium chloride

Product 1

HCID 57125215HCID 57125215, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-phenylpropanol (2.68 g., 20 mmole), triphenyl-(2-keto-n-heptyl)phosphonium chloride (8.22 g., 20 mmole), sodium carbonate (2.36 g., 22.3 mmole) and water (20 ml.) in tetrahydrofuran (70 ml.) is refluxed for 6 hours under an atmosphere of argon. The cooled mixture is diluted with ethyl ether and the layer separate. The organic phase is washed with saturated sodium chloride solution, dried over Na2SO4 and evaporated. The residue is taken up in hexane and insoluble triphenyl phosphine oxide is filtered off. The residue obtained on evaporation of the hexane is purified by flash chromatography on silica gel (120 g.) eluting with ethyl ether/hexane (1:30) to give two isomers of 1-phenyl-3-decen-5-one; 2.93 g. Rf (ethyl ether/hexane 1:4) 0.73 and 0.42 g. Rf (ethyl ether/hexane 1:4) 0.85.

Workup

  1. temperatureis refluxed for 6 hours under an atmosphere of argon
  2. customthe layer separate
  3. washThe organic phase is washed with saturated sodium chloride solution
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. filtrationinsoluble triphenyl phosphine oxide is filtered off
  7. customThe residue obtained on evaporation of the hexane
  8. customis purified by flash chromatography on silica gel (120 g.)
  9. washeluting with ethyl ether/hexane (1:30)

Sources & evidence

ORD record
ord-a62468c002b44c688994bfdb4c284df2
Source dataset
uspto-grants-1983_11
Patent number
US04416833

Reaction notes

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