Sodium Carbonate → Triphenyl(3-pyridylmethyl)phosphonium chloride

HRID 2054179Notes

Reaction equation

HRID 2054179 reaction equation
C([O-])([O-])=O.[Na+].[Na+].Cl.[Cl:8][CH2:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1.[C:16]1([P:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O.C1(C)C=CC=CC=1>[Cl-:8].[C:29]1([P+:22]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 233943-(Chloromethyl)pyridine hydrochloride

Product 1

HCID 22325077Triphenyl(3-pyridylmethyl)phosphonium chloride

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

To an ice-cooled 2-phase mixture of 55.8 g (195 mmol) Na2CO3.10 H2O in 200 ml water and 100 ml toluene, 21.3 g (133 mmol) 3-chloromethylpyridine hydrochloride is added in portions. The mixture is stirred at 0° C. until a clear solution is obtained, the aqueous phase separated off, and the mixture extracted twice with 50 ml toluene. The toluene phases are dried (Na2SO4) and evaporated in the RE (10 mbar, 30° C.) to about half its original volume. To the yellowish solution, 68.1 g (259 mmol) triphenylphosphine is added and the mixture stirred for several days under a N2 atmosphere at 70° C. The title compound is precipitated off in the process. It is filtered off and washed with toluene and hexane; 1H-NMR (DMSO-6) 8.47 (m, 1HPy), 8.18 (sb, 1HPy), 7.91 (m, 3H), 7.72 (m, 12H), 7.37 (m, 1HPy), 7.26 (m, 1HPy), 5.33 (d, J=15 Hz, H2C); FAB-MS (M-Cl)+=354; an. calc. (C24H21NClP.0.17 H2O) C, 73.36%; H, 5.47%; N, 3.56%; Cl, 9.02%; P, 7.88%; H2O, 0.78%; meas. C, 73.11%; H, 5.43%; N, 3.82%; Cl, 9.49%; P, 7.98%; H2O, 0.77%.

Workup

  1. customis obtained
  2. customthe aqueous phase separated off
  3. extractionthe mixture extracted twice with 50 ml toluene
  4. dry with materialThe toluene phases are dried (Na2SO4)
  5. customevaporated in the RE (10 mbar, 30° C.) to about half its original volume
  6. stirringthe mixture stirred for several days under a N2 atmosphere at 70° C
  7. customThe title compound is precipitated off in the process
  8. filtrationIt is filtered off
  9. washwashed with toluene and hexane

Sources & evidence

ORD record
ord-740a03fa36f540719a6df1cb0513c7af
Source dataset
uspto-grants-2008_02
Patent number
US07329660B2

Reaction notes

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