1-Methylimidazole → HCID 178480871, compound

HRID 2104469Notes

Reaction equation

FC([P:8](=[O:23])([C:16]([F:22])([F:21])[C:17]([F:20])([F:19])[F:18])[C:9]([F:15])([F:14])[C:10]([F:13])([F:12])[F:11])(F)C(F)(F)F.P(C(C(F)(F)F)(F)F)(C(C(F)(F)F)(F)F)C(C(F)(F)F)(F)F.[CH3:46][N:47]1[CH:51]=[CH:50][N:49]=[CH:48]1.[F:52][C:53]([F:64])([C:57]([F:63])([F:62])[C:58]([F:61])([F:60])[F:59])[CH2:54][CH2:55][OH:56]>C1C=CC=CC=1>[F:22][C:16]([P:8]([C:9]([F:14])([F:15])[C:10]([F:13])([F:12])[F:11])(=[O:56])[O-:23])([F:21])[C:17]([F:18])([F:19])[F:20].[F:52][C:53]([F:64])([C:57]([F:63])([F:62])[C:58]([F:61])([F:60])[F:59])[CH2:54][CH2:55][N+:49]1[CH:50]=[CH:51][N:47]([CH3:46])[CH:48]=1

Participants

Conditions

Temperature: 100 °C

Procedure

8.27 g (20.5 mmol) of tris(pentafluoroethyl)phosphine oxide, (C2F5)3P═O, are mixed with 20 cm3 of dry benzene and 1.67 g (20.3 mmol) of N-methylimidazole in a flask fitted with a reflux condenser held at minus 25° C. 4.37 g (20.4 mmol) of 3,3,4,4,5,5,5-heptafluoropentan-1-ol are added to this mixture at room temperature while stirring using a magnetic stirrer. The reaction mixture is heated at an oil-bath temperature of 100° C. for 20 minutes. After cooling to room temperature, the phosphinate is separated from the benzene phase and washed twice with 10 cm3 of benzene. Drying at 60° C. (2 hours) under a vacuum of 13.3 Pa gives 11.55 g of 1-(3,3,4,4,5,5,5-heptafluoropentyl)-3-methylimidazolium bis(pentafluoroethyl)phosphinate as liquid. The yield is 97.5%.

Workup

customfitted with a reflux condenser
custom25° C
temperatureAfter cooling to room temperature
customthe phosphinate is separated from the benzene phase
washwashed twice with 10 cm3 of benzene
customDrying at 60° C. (2 hours) under a vacuum of 13.3 Pa

Sources & evidence

ORD record: ord-8649ed5baa454c67ad07a0505054ec10
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576242B2

Reaction notes

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