Potassium Carbonate → Triphenyl(3-pyridylmethyl)phosphonium chloride

HRID 1819992Notes

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

Participants

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

extractionThe resulting mixture was extracted three times with diethyl ether
washwashed twice with brine
customdried
concentrationconcentrated
temperaturecooled to ambient temperature
filtrationThe solid product was filtered
washwashed with toluene
customdried under vacuum

Sources & evidence

ORD record: ord-b621ea42e69347ef9c7999e1c3f0f15e
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601874B2

Reaction notes

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