Reaktion #61939

Reaktionsgleichung

6-allyloxy-3-methyl-4-trifluoromethanesulfonyloxy-phthalic acid dimethyl ester

diethylamine

→

desired product

Ausbeute 55.0%

6-Hydroxy-3-methyl-4-trifluoromethanesulfonyloxy-phthalic acid dimethyl ester

Ausbeute 55.0%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas consumed
2. 2
   SonstigeThe crude reaction mixture
3. 3
   Sonstigewas partitioned between diethyl ether and HCl (0.1 N)
4. 4
   WaschenThe organic layer was washed with brine
5. 5
   Trocknendried over sodium sulfate
6. 6
   FiltrationFiltration and evaporation of solvents in vacuo
7. 7
   Sonstigeyielded a crude material, which
8. 8
   Sonstigewas purified by silica gel chromatography

Vorschrift

To a solution of 6-allyloxy-3-methyl-4-trifluoromethanesulfonyloxy-phthalic acid dimethyl ester (8.39 g, 20.3 mmol) in toluene (20 mL) was added tetrakistriphenylphosphine palladium (0.47 g, 0.40 mmol) and diethylamine (2.97 g, 40.86 mmol) at room temperature under an atmosphere of nitrogen. Stirring at room temperature was continued until all starting material was consumed. The crude reaction mixture was partitioned between diethyl ether and HCl (0.1 N). The organic layer was washed with brine and dried over sodium sulfate. Filtration and evaporation of solvents in vacuo yielded a crude material, which was purified by silica gel chromatography to provide 4.16 g (55%) of the desired product as an off-white solid. 1H NMR (300 MHz, CDCl3): δ=2.20 (s, 3H), 3.93 (s, 3H), 3.95 (s, 3H), 7.01 (s, 1H) ppm; 19F NMR (282 MHz, CDCl3): δ=−74 ppm.

Quelle