Water → HCID 57125215, compound

HRID 1702433Notes

Reaction equation

HRID 1702433 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 layers 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 layers 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-c514962ff0134e43bbe47b1fb8810501
Source dataset
uspto-grants-1983_04
Patent number
US04381297

Reaction notes

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