Reacción #8295

Ecuación de reacción

2,5-dihydrofuran

Methanol

sodium nitrite

ethyl 4-aminobenzoate

tetrafluoroboric acid

→

title compound

4-(5-Methoxy-tetrahydro-furan-3-yl)-benzoic acid ethyl ester

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe mixture refluxed for 30 min
2. 2
   FiltraciónThe mixture is filtered through Celite® pad
3. 3
   workup.ADDITIONthe filtrate diluted with dichloromethane (100 mL)
4. 4
   OtroThe organic layer is separated
5. 5
   Concentraciónconcentrated in vacuo
6. 6
   OtroThe residue is chromatographed on SiO2 (10% ethyl acetate/hexanes)

Procedimiento

A solution of sodium nitrite (1.67 g, 24.2 mmol) in water (14 mL) is added dropwise to an ice cold mixture of ethyl 4-aminobenzoate (4.0 g, 24.2 mmol) and tetrafluoroboric acid (7.8 mL, 48%, 59.78 mmol) and stirred for 30 min. Methanol (28.5 mL), 2,5-dihydrofuran (3.66 mL, 48.4 mmol) and palladium(II) acetate (70 mg, 0.31 mmol) are added and the mixture refluxed for 30 min. The mixture is filtered through Celite® pad and the filtrate diluted with dichloromethane (100 mL). The organic layer is separated and concentrated in vacuo. The residue is chromatographed on SiO2 (10% ethyl acetate/hexanes) to yield the title compound, 2.45 g (42%), as a white solid.

Fuente