Triphenylphosphine → 5-Ethoxycarbonylpenta-2,4-dienyltriphenylphosphonium bromide

HRID 372127Notes

Reaction equation

HRID 372127 reaction equation
[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:20][CH2:21][CH:22]=[CH:23][CH:24]=[CH:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>C1C=CC=CC=1>[Br-:20].[CH2:29]([O:28][C:26]([CH:25]=[CH:24][CH:23]=[CH:22][CH2:21][P+:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:27])[CH3:30]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 54103448Ethyl 6-bromohexa-2,4-dienoate

Product 1

HCID 736763405-Ethoxycarbonylpenta-2,4-dienyltriphenylphosphonium bromideYield 64.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a stirred solution of triphenylphosphine (34 g.) in dry benzene (300 ml.) was added ethyl 6-bromohexa-2,4-dienoate (30 g.). After 18 hours, the benzene was decanted from the precipitated paste which solidified on adding diethyl ether and was ground up and filtered to give 5-ethoxycarbonylpenta-2,4-dienyltriphenylphosphonium bromide (40 g.), m.p. 139°-144° C.

Workup

  1. customthe benzene was decanted from the precipitated paste which
  2. additionon adding diethyl ether
  3. filtrationfiltered

Sources & evidence

ORD record
ord-daeb95e192a0405aa40259fcc570a5cd
Source dataset
uspto-grants-1978_05
Patent number
US04088821

Reaction notes

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