Trioctylamine → Trioctylpropargylammonium bis(pentafluoroethyl)phosphinate

HRID 2173701Notes

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].[CH2:21]([N:29]([CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>>[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].[CH2:38]([N+:29]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:12][C:11]#[CH:10])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45]

Participants

Reactant 2

HCID 14227Trioctylamine

HCID 89783114Propargyl bis(pentafluoroethyl)phosphinate

Product 1

HCID 89783214Trioctylpropargylammonium bis(pentafluoroethyl)phosphinateYield 91%

Procedure

Propargyl bis(pentafluoroethyl)phosphinate (4.131 g; 12.1 mmol) is slowly added dropwise to cooled (0° C.) trioctylamine (4.333 g; 12.3 mmol) in a 100 ml glass flask. An orange, more highly viscous solution forms spontaneously, which is warmed to room temperature. The readily volatile constituents are removed in vacuo (10−3 mbar) at room temperature to 120° C. Trioctylpropargylammonium bis(pentafluoroethyl)phosphinate, [(C8H17)3—NCH2C≡CH][(C2F5)2P(O)O], (7.646 g; 11.0 mmol) is isolated as pale-orange liquid in a yield of 91% and a purity of 97%.

Workup

customThe readily volatile constituents are removed in vacuo (10−3 mbar) at room temperature to 120° C

Sources & evidence

ORD record: ord-410a8812b3964bc4b243d58d98022110
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056881B2

Reaction notes

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