6-Chloro-1-(triphenyl-lambda~5~-phosphanylidene)hexan-2-one → [(tetrahydro-2H-pyran-2-ylidene)methyl]triphenylphosphonium chloride

HRID 441602

Reaction equation

HRID 441602 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([CH: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]>C1C=CC=CC=1>[Cl-:1].[O:7]1[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1=[CH: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

Participants

3

Reactant 1

HCID 203690016-Chloro-1-(triphenyl-lambda~5~-phosphanylidene)hexan-2-one

Product 1

HCID 73680070[(tetrahydro-2H-pyran-2-ylidene)methyl]triphenylphosphonium chloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution containing 20 parts of (5-chloropentanoylmethylene)triphenylphosphorane in 200 parts of benzene is heated at the reflux temperature for about 16 hours. Cooling of this solution results in crystallization of a product which is isolated by filtration to afford [(tetrahydro-2H-pyran-2-ylidene)methyl]triphenylphosphonium chloride. This product is characterized by 60-MHz nuclear magnetic resonance peaks in CDCl3 (deuterated chloroform) at about 107 cps (multiplet), 170 cps (multiplet), 228 cps (multiplet) and 329 cps (doublet, J≃ 18 cps) in addition to the aromatic protons. This compound melts at about 215°-221° C. and is represented by the following structure: ##STR8##

Workup

  1. temperatureis heated at the reflux temperature for about 16 hours
  2. temperatureCooling of this solution
  3. customresults in crystallization of a product which
  4. customis isolated by filtration

Sources & evidence

ORD record
ord-bcdf88b650e24a1aa85f099188c2612f
Source dataset
uspto-grants-1977_08
Patent number
US04041050

Linked notes

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