Reaction #4031

Reaction equation

Methyl perfluorobutyrate

sodium trimethylsilanolate

→

sodium perfluorobutyrate

Yield 84.0%

Solvents

ether

Conditions

Workup

1. 1
   FiltrationThe solid was filtered under nitrogen
2. 2
   Washwashed with dry ether
3. 3
   Otherdried under a stream of nitrogen

Procedure

Methyl perfluorobutyrate (12.81 g, 56 mmol) was added dropwise to a stirred solution of sodium trimethylsilanolate (6.3 g, 56 mmol) in dry ether (300 mL) at room temperature under nitrogen. The reaction mixture was stirred overnight. The solid was filtered under nitrogen, washed with dry ether, and dried under a stream of nitrogen to afford sodium perfluorobutyrate (11.1 g, 84% yield) as a white solid: 19F NMR (D2O) δ -79.6 (t, J=8 Hz, CF3 --, 3F), -117.2 (q, J=8 Hz, CF3CF2CF2 --, 2F), -126.2 ppm (s, CF3CF2 --, 2F). Anal. Calcd. for C4F7NaO2 : C, 20.36; F, 56.35; Na, 9.74. Found: C, 20.84, 20.61, 20.58; F, 56.68, 53.24; Na, 9.89, 9.65.

Source