Triphenylphosphine → Triphenyl(3-pyridylmethyl)phosphonium chloride

HRID 496066Notes

Reaction equation

HRID 496066 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.Cl.[N:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27][Cl:28])[CH:22]=1>CN(C)C=O>[Cl-:28].[C:14]1([P+:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:27][C:23]2[CH:22]=[N:21][CH:26]=[CH:25][CH:24]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 233943-(Chloromethyl)pyridine hydrochloride

Product 1

HCID 22325077Triphenyl(3-pyridylmethyl)phosphonium chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
5 °C

Procedure

13.1 g of triphenyphosphine are added to a solution of 8.2 g of 3-picolyl chloride hydrochloride in 120 ml of dimethylformamide. After stirring for 5 minutes, the mixture is heated at reflux for 30 minutes in a microwave apparatus and then cooled to 5° C. The crystals obtained are filtered off, rinsed with dimethylformamide and then with ether, and dried under reduced pressure, allowing the expected product to be isolated.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 30 minutes in a microwave apparatus
  3. customThe crystals obtained
  4. filtrationare filtered off
  5. washrinsed with dimethylformamide
  6. dry with materialwith ether, and dried under reduced pressure
  7. customto be isolated

Sources & evidence

ORD record
ord-cdcd86a29f9a48d5935f932b22154baa
Source dataset
uspto-grants-2005_09
Patent number
US06943184B2

Reaction notes

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