Potassium Carbonate → Phosphonium, triphenyl(2-pyridinylmethyl)-, chloride

HRID 1188256Notes

Reaction equation

Cl.[Cl:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=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.O1CCOCC1>[Cl-:2].[N:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH2:3][P+:22]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:19]1[CH:18]=[CH:17][CH:16]=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a stirred solution of 2-(chloromethyl)pyridine hydrochloride (8.0 g, 48.8 mmol) in water (20 mL) was added K2CO3 (6.74 g, 48.7 mmol) portionwise. The resulting mixture was extracted four times with diethyl ether. The extracts were combined and washed twice with brine, dried and concentrated. The residue (5.78 g, 45.3 mmol) was dissolved in 1,4-dioxane (19 mL) and Ph3P (11.89 g, 45.3 mmol) was added. The mixture was heated at 110° C. overnight and then cooled to ambient temperature. The solid product was filtered, washed with ether, and dried under vacuum to give (2-pyridylmethyl)triphenylphosphonium chloride (15.78 g, 83%) as a pale solid.

Workup

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

Sources & evidence

ORD record: ord-85662297677446f9b2b97d32e41a289f
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673975B2

Reaction notes

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