Reacción #57615

Ecuación de reacción

sodium percarbonate

3-methyl-4-vinyl-1-benzofuran-2-carboxylate

3-methyl-4-vinylbenzofuran-2-carboxylic acid ethyl ester

borane THF

Water

water

→

ethyl 4-(2-hydroxyethyl)-3-methyl-1-benzofuran-2-carboxylate

Rendimiento 80.6%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction was cooled in an ice bath
2. 2
   TemperaturaThe reaction was heated at ˜50° C. for 1 hour
3. 3
   Temperaturacooled to room temperature
4. 4
   Extracciónthe resulting mixture was extracted with ethyl acetate
5. 5
   LavadoThe organic layer washed with water and brine
6. 6
   Secadodried over sodium sulfate
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated in vacuo
9. 9
   OtroThe residue was chromatographed on silica gel eluting with hexane/ethyl acetate (2:1)

Procedimiento

To a solution of 0.35 g (1.5 mmol) of 3-methyl-4-vinyl-1-benzofuran-2-carboxylate (Example 87, Step 1) in 3 mL of THF, cooled in an ice bath, was added 1 mL (1 mmol) of borane-THF complex (1.0M solution in THF). The reaction was stirred at room temperature for 2 hours. The reaction was cooled in an ice bath and 1.5 mL of water was added. Next 0.61 g of sodium percarbonate was added in one portion. The reaction was heated at ˜50° C. for 1 hour, then cooled to room temperature. Water was added and the resulting mixture was extracted with ethyl acetate. The organic layer washed with water and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel eluting with hexane/ethyl acetate (2:1) to provide 0.20 g of ethyl 4-(2-hydroxyethyl)-3-methyl-1-benzofuran-2-carboxylate. Yield 54%. m.p. 88-90° C.; MS 249.1 (M+H)+.

Fuente