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Potassium Carbonate → Triphenyl(3-pyridylmethyl)phosphonium chloride

HRID 660470
Notes
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Reaction equation

HRID 660470 reaction equation
Cl.[Cl:2][CH2:3][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1.C([O-])([O-])=O.[K+].[K+].[CH:16]1[CH:21]=[CH:20][C:19]([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:18][CH:17]=1>O.C1(C)C(C)=CC=CC=1>[Cl-:2].[N:6]1[CH:7]=[CH:8][CH:9]=[C:4]([CH2:3][P+:22]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:19]2[CH:18]=[CH:17][CH:16]=[CH:21][CH:20]=2)[CH:5]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 233943-(Chloromethyl)pyridine hydrochloride

Product 1

HCID 22325077Triphenyl(3-pyridylmethyl)phosphonium chlorideYield 58.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 7237
O-Xylene
Solvent

Conditions

Temperature
133.5 °C

Procedure

To a stirred solution of 3-(chloromethyl)pyridine hydrochloride (5.17 g, 31.5 mmol) in water (8 mL) was added K2CO3 (4.34 g, 31.5 mmol) portionwise. The resulting mixture was extracted three times with diethyl ether. The extracts were combined and washed twice with brine, dried and concentrated. The residue (3.25 g, 25.5 mmol) was dissolved in xylene (30 mL) and Ph3P (6.70 g, 25.5 mmol) was added. The mixture was heated at 133-134° C. overnight and then cooled to ambient temperature. The solid product was filtered, washed with toluene, and dried under vacuum to give (3-pyridylmethyl)triphenylphosphonium chloride (5.86 g, 48%) as a pinkish solid.

Workup

  1. extractionThe resulting mixture was extracted three times with diethyl ether
  2. washwashed twice with brine
  3. customdried
  4. concentrationconcentrated
  5. temperaturecooled to ambient temperature
  6. filtrationThe solid product was filtered
  7. washwashed with toluene
  8. customdried under vacuum

Sources & evidence

ORD record
ord-3520a4f885da4c69b3a60819f31f89ec
Source dataset
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08084503B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes