Triphenylphosphine → Triphenyl[(quinolin-2-yl)methyl]phosphanium chloride

HRID 892145Notes

Reaction equation

[Cl:1][CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.[C:13]1([P:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(#N)C.CCOCC>[Cl-:1].[C:26]1([P+:19]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:2][C:3]2[CH:12]=[CH:11][C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[N:4]=2)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2-chloromethyl-quinoline (2.9 g, 20 mmol) in acetonitrile (32 mL) is added triphenylphosphine (4.49 g, 17 mmol). The resulting mixture is warmed to 60° C. and stirred at this temperature for 15 h. This mixture is cooled, diluted with ether, then filtered. The solid is washed with ether, then dried under high vacuum to give the title compound as a solid. 1H NMR (300 MHz, CDCl3) δ 8.20 (d, 1H), 8.06 (d, 1H), 7.95 (m, 6H), 7.42–7.8 (m, 13H), 6.10 (d, 2H).

Workup

temperatureThis mixture is cooled
filtrationfiltered
washThe solid is washed with ether
customdried under high vacuum

Sources & evidence

ORD record: ord-bcd707aada694e4a99c24eac724329cc
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07005440B1

Reaction notes

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