Triphenylphosphine → [(2-Ethyl-1,3-oxazol-4-yl)methyl]triphenylphosphonium chloride

HRID 2221599Notes

Reaction equation

HRID 2221599 reaction equation
[Cl:1][CH2:2][C:3]1[N:4]=[C:5]([CH2:8][CH3:9])[O:6][CH:7]=1.[C:10]1([P:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(#N)C>[Cl-:1].[CH2:8]([C:5]1[O:6][CH:7]=[C:3]([CH2:2][P+:16]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:4]=1)[CH3:9]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 23076478HCID 23076478, compound

Product 1

HCID 23076591[(2-Ethyl-1,3-oxazol-4-yl)methyl]triphenylphosphonium chlorideYield 81%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-chloromethyl-2-ethyl-1,3-oxazole (2.90 g), triphenylphosphine (5.22 g) and acetonitrile (100 mL) was heated under reflux for 15 hrs. After concentration of the reaction mixture, the precipitated crystals were washed with diethyl ether to give [(2-ethyl-1,3-oxazol-4-yl)methyl]triphenylphosphonium chloride as colorless crystals (6.57 g, yield 81%). Recrystallization from acetonitrile-diethyl ether gave colorless prism crystals. melting point: 223-224° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 15 hrs
  3. washAfter concentration of the reaction mixture, the precipitated crystals were washed with diethyl ether

Sources & evidence

ORD record
ord-ae63e386c8b547d1b115c760e2d509a9
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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