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

HRID 30648Notes

Reaction equation

HRID 30648 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 81.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-chloromethyl-2-ethyl-1,3-oxazole (4.87 g), triphenylphosphine (7.89 g) and acetonitrile (100 mL) was heated under reflux for 15 hrs. The reaction mixture was concentrated, and the obtained crystals were washed with diethyl ether to give [(2-ethyl-1,3-oxazol-4-yl)methyl]triphenylphosphonium chloride as colorless crystals (10.02 g, yield 79%). Recrystallization thereof from acetonitrile-diethyl ether gave colorless prism crystals. melting point: 222-223° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 15 hrs
  3. concentrationThe reaction mixture was concentrated
  4. washthe obtained crystals were washed with diethyl ether

Sources & evidence

ORD record
ord-5aeef27d4d004c86b81cdd842521616d
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Reaction notes

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