1-Methylpyrrolidine → 1-Methyl-1-propargylpyrrolidinium bis(pentafluoro-ethyl)phosphinate

HRID 2173700Notes

Reaction equation

[F:1][C:2]([P:8]([C:14]([F:20])([F:19])[C:15]([F:18])([F:17])[F:16])(=[O:13])[O:9][CH2:10][C:11]#[CH:12])([F:7])[C:3]([F:6])([F:5])[F:4].[CH3:21][N:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1>CCCCCC>[F:7][C:2]([P:8]([C:14]([F:19])([F:20])[C:15]([F:18])([F:17])[F:16])(=[O:9])[O-:13])([F:1])[C:3]([F:6])([F:5])[F:4].[CH3:21][N+:22]1([CH2:10][C:11]#[CH:12])[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

Conditions

Temperature: 0 °C

Procedure

Propargyl bis(pentafluoroethyl)phosphinate (6.44 g; 18.9 mmol) is added to cooled (0° C.) N-methylpyrrolidine (1.60 g; 18.7 mmol) in a 25 ml glass flask. In an exothermic reaction, a yellow solid forms spontaneously. This is suspended in n-hexane (12 ml), stirred at 0° C. for 30 minutes, warmed (room temperature), diluted with further n-hexane (8 ml) and stirred at room temperature for 17 h. The readily volatile constituents are removed in vacuo (10−3 mbar) at 50° C. 1-Methyl-1-propargylpyrrolidinium bis(pentafluoro-ethyl)phosphinate, [CH≡CCH2MPL][(C2F5)2P(O)O], (7.47 g; 17.6 mmol) is isolated as pale-beige solid in a yield of 94% and a purity of 98%.

Workup

customIn an exothermic reaction
temperaturewarmed (room temperature)
stirringstirred at room temperature for 17 h
customThe readily volatile constituents are removed in vacuo (10−3 mbar) at 50° C

Sources & evidence

ORD record: ord-aa7630685ca94da1881906306df04d9a
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056881B2

Reaction notes

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