Triphenylphosphine → Pentadec-2-ynyl-triphenylphosphonium bromide

HRID 622107Notes

Reaction equation

HRID 622107 reaction equation
[Br:1][CH2:2][C:3]#[C:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[C:17]1([P:23]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CCOCC>[Br-:1].[CH2:2]([P+:23]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:3]#[C:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 150032421-Bromopentadec-2-yne

Product 1

HCID 21293732Pentadec-2-ynyl-triphenylphosphonium bromide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1-Bromo-2-pentadecyne (0.01 mole) and triphenylphosphine (0.01 mole) are mixed in ether to give pentadec-2-ynyl-triphenylphosphonium bromide. The salt (0.01 mole) is dissolved in absolute ethanol containing one equivalent of sodium ethoxide. Ethyl 5-oxopentanoate (0.01 mole) is added and the mixture is refluxed for 24 hours to give a mixture of cis-and-trans ethyl 5-eicosen-7-ynoate. The isomers are separated by chromatography and the trans isomer is converted to 5-hydroxy-6-(1,4-dimethyl-5-carboxy-2-imidazolylthio)-7-eicosynoic acid as described in Example 14(c).

Sources & evidence

ORD record
ord-0a7f1160a2054bbe8cbd933618c7b74e
Source dataset
uspto-grants-1988_09
Patent number
US04769386

Reaction notes

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