1-Methylimidazole → 3-[2-(Allyloxy)ethyl]-1-methylimidazolium bis(pentafluoroethyl)phosphinate

HRID 2173696Notes

Reaction equation

HRID 2173696 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].[CH3:24][N:25]1[CH:29]=[CH:28][N:27]=[CH:26]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:27]1[CH:28]=[CH:29][N+:25]([CH3:24])=[CH:26]1)[CH:14]=[CH2:15]

Participants

3

Reactant 2

HCID 13901-MethylimidazoleHCID 897829122-(Allyloxy)ethyl bis(pentafluoroethyl)phosphinate2×

Product 1

HCID 897829923-[2-(Allyloxy)ethyl]-1-methylimidazolium bis(pentafluoroethyl)phosphinate

Conditions

Temperature
0 °C

Procedure

2-(Allyloxy)ethyl bis(pentafluoroethyl)phosphinate, (C2F5)2P(O)OCH2CH2—OCH2CH═CH2, (4.135 g; 10.7 mmol) is slowly added dropwise to dry and cooled (0° C.) N-methylimidazole (0.793 g; 9.7 mmol) (exothermic) in a 50 ml glass flask. A pale-yellow, more highly viscous solution forms spontaneously, which is stirred at 0° C. for 1.5 h, warmed and stirred at room temperature for 5 h. The readily volatile constituents are removed in vacuo (10−3 mbar) at room temperature. 3-[2-(Allyloxy)ethyl]-1-methylimidazolium bis(pentafluoroethyl)phosphinate, [CH2═CHCH2OCH2CH2MIM][(C2F5)2—P(O)O], (4.521 g; 9.7 mmol) is isolated as highly viscous, pale-yellow liquid in quantitative yield and a purity of 94%.

Workup

  1. customto dry
  2. temperaturewarmed
  3. stirringstirred at room temperature for 5 h
  4. customThe readily volatile constituents are removed in vacuo (10−3 mbar) at room temperature

Sources & evidence

ORD record
ord-a17cb3ba23e94d55904f8d37e8539c67
Source dataset
uspto-grants-2015_06
Patent number
US09056881B2

Reaction notes

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