Pyridine → N-[2-(Allyloxy)ethyl]pyridinium bis(pentafluoroethyl)phosphinate

HRID 2173695Notes

Reaction equation

HRID 2173695 reaction equation
[F:1][C:2]([P:8]([C:17]([F:23])([F:22])[C:18]([F:21])([F:20])[F:19])(=[O:16])[O:9][CH2:10][CH2:11][O:12][CH2:13][CH:14]=[CH2:15])([F:7])[C:3]([F:6])([F:5])[F:4].[N:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[F:7][C:2]([P:8]([C:17]([F:22])([F:23])[C:18]([F:21])([F:20])[F:19])(=[O:9])[O-:16])([F:1])[C:3]([F:6])([F:5])[F:4].[CH2:13]([O:12][CH2:11][CH2:10][N+:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:14]=[CH2:15]

Participants

3

Reactant 2

HCID 1049PyridineHCID 897829122-(Allyloxy)ethyl bis(pentafluoroethyl)phosphinate2×

Product 1

HCID 89783222N-[2-(Allyloxy)ethyl]pyridinium bis(pentafluoroethyl)phosphinate

Conditions

Temperature
0 °C

Procedure

2-(Allyloxy)ethyl bis(pentafluoroethyl)phosphinate, (C2F5)2P(O)O—CH2CH2OCH2CH═CH2, (2.407 g; 6.2 mmol) is slowly added dropwise to dry and cooled (0° C.) pyridine (0.502 g; 6.3 mmol) in a 25 ml glass flask. An orange, more highly viscous solution forms spontaneously, which is stirred at 0° C. for 1 h, warmed and stirred at room temperature for 2 h. The readily volatile constituents are removed in vacuo (10−3 mbar) at room temperature. N-[2-(Allyloxy)ethyl]pyridinium bis(pentafluoroethyl)phosphinate, [CH2═CHCH2OCH2CH2Py][(C2F5)2P(O)O], is isolated (2.829 g; 6.1 mmol) as highly viscous, intensely red-brown liquid in quantitative yield and a purity of 89%.

Workup

  1. customto dry
  2. temperaturewarmed
  3. stirringstirred at room temperature for 2 h
  4. customThe readily volatile constituents are removed in vacuo (10−3 mbar) at room temperature

Sources & evidence

ORD record
ord-1f42b9354d774ea0b9264e224d341fc8
Source dataset
uspto-grants-2015_06
Patent number
US09056881B2

Reaction notes

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