Propargyl alcohol → Propargyl bis(pentafluoroethyl)phosphinate

HRID 2173698Notes

Reaction equation

HRID 2173698 reaction equation
[F-].[K+].[F:3][C:4]([P:10](=[O:25])(C(F)(F)C(F)(F)F)[C:11]([F:17])([F:16])[C:12]([F:15])([F:14])[F:13])([F:9])[C:5]([F:8])([F:7])[F:6].[CH2:26]([OH:29])[C:27]#[CH:28]>>[P:10]([O:29][CH2:26][C:27]#[CH:28])([C:4]([C:5]([F:6])([F:7])[F:8])([F:3])[F:9])([C:11]([C:12]([F:15])([F:14])[F:13])([F:17])[F:16])=[O:25]

Participants

4

Reactant 3

HCID 7859Propargyl alcoholHCID 522689Potassium FluorideHCID 11165593tris(pentafluoroethyl)phosphine Oxide

Product 1

HCID 89783114Propargyl bis(pentafluoroethyl)phosphinate

Procedure

Potassium fluoride (0.262 g; 4.5 mmol) is suspended in cooled (0° C.) tris(pentafluoroethyl)phosphine oxide (14.930 g; 37.0 mmol) in a 100 ml glass flask, and propargyl alcohol (2.055 g; 36.7 mmol) is added. The yellow reaction solution is slowly warmed (about 6 h) and stirred at room temperature for 19.5 h. Volatile components are removed in vacuo (10−3 mbar) at 0° C. After recondensation in vacuo (10−3 mbar) at room temperature, propargyl bis(pentafluoroethyl)phosphinate, (C2F5)2P(O)OCH2C≡CH, is isolated as clear and colourless liquid (7.831 g; 23.0 mmol) in a yield of 63% and a purity of 95%. The ester becomes a brown colour after a few minutes at room temperature and is therefore stored at 3° C.

Workup

  1. temperatureThe yellow reaction solution is slowly warmed (about 6 h)
  2. customVolatile components are removed in vacuo (10−3 mbar) at 0° C
  3. customAfter recondensation in vacuo (10−3 mbar) at room temperature

Sources & evidence

ORD record
ord-f8aa48e79a7141caa036852e8d77418f
Source dataset
uspto-grants-2015_06
Patent number
US09056881B2

Reaction notes

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