Tetrabutylammonium Fluoride → methyl 3-fluoro-2,2-dimethylpropanoate
Reaction equation
[F-:1].C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:19][O:20][C:21](=[O:34])[C:22]([CH3:33])([CH3:32])[CH2:23]OS(C(F)(F)F)(=O)=O>C1COCC1>[CH3:19][O:20][C:21](=[O:34])[C:22]([CH3:33])([CH3:32])[CH2:23][F:1]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
27 mL of a 1 M solution of tetrabutylammonium fluoride in THF are added slowly and under ice cooling to a solution of 7.25 g (27.4 mmol) 2,2-dimethyl-3-trifluoromethanesulfonyloxy-propionic acid methyl ester in 150 mL of THF. The resulting solution is stirred 6 h at 0° C. and then 10 h at RT. The solvent is evaporated carefully and the residue partitioned between DCM and brine. The organic phase is washed with brine, dried with sodium sulfate and evaporated carefully. The brown oil is distilled in a Kugelrohr-oven (oven temperature 120 to 150° C.) to give the title compound as a colorless liquid.