Reacción #3868

Ecuación de reacción

sodium borohydride

product

7-Methoxy-2,2-dimethyl-3-benzofuranone

→

7-Methoxy-3-hydroxy-2,2-dimethylbenzofuran

Disolventes

methylene chloride

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroevaporated in vacuo
2. 2
   Otrotoluene, the layers are separated
3. 3
   Lavadothe organic phase washed
4. 4
   Otrodried
5. 5
   Otroevaporated in vacuo
6. 6
   Otroaffording an oil which
7. 7
   Otrodried
8. 8
   Filtraciónfiltered
9. 9
   Otroevaporated in vacuo
10. 10
    workup.DISSOLUTIONThe residue is dissolved in ethyl acetate
11. 11
    Otrochromatographed on silica gel affording the desired product as a white solid

Procedimiento

An aqueous solution of sodium borohydride (8.2 g, 50 ml) is added to a stirred solution of the product obtained in Step 3. (41.8 g) in ethanol (1 l) and the mixture refluxed for 3 hours and evaporated in vacuo. The residue is taken up in water and toluene, the layers are separated and the organic phase washed, dried and evaporated in vacuo affording an oil which is dissolved in methylene chloride, dried, filtered and evaporated in vacuo. The residue is dissolved in ethyl acetate and chromatographed on silica gel affording the desired product as a white solid.

Fuente