Reacción #9402

Ecuación de reacción

TBSCl

14

3-(3′-hydroxy-4′-methoxyphenyl)-6-methoxybenzo[b]furan

Et3N

→

benzo[b]furan

Rendimiento 92.2%

3-(3′-tert-Butyldimethylsilyloxy-4′-methoxyphenyl)-6-methoxybenzo[b]furan

Rendimiento 92.2%

Disolventes

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroallowing too reach room temperature
2. 2
   OtroThe reaction was quenched with water
3. 3
   Otrothe phases separated
4. 4
   Extracciónthe aqueous phase was extracted with CH2Cl2 (3×30 mL)
5. 5
   SecadoThe combined organic solutions were dried over MgSO4
6. 6
   Concentraciónconcentrated under reduced pressure
7. 7
   OtroPurification
8. 8
   Lavadoby flash column chromatography (silica gel, elution with hexanes)

Procedimiento

To a solution of 14 (3.51 g, 12.9 mmol) in CH2Cl2 (30 mL), under nitrogen, was added Et3N (1.98 mL, 14.2 mmol) followed by DMAP (0.162 g, 14.2 mmol) and TBSCl (2.4 g, 14.2 mmol) at 0° C. The reaction mixture was stirred for 12 h allowing too reach room temperature. The reaction was quenched with water, the phases separated, and the aqueous phase was extracted with CH2Cl2 (3×30 mL). The combined organic solutions were dried over MgSO4 and concentrated under reduced pressure. Purification by flash column chromatography (silica gel, elution with hexanes) afforded 4.57 g (11.9 mmol, 92%) of the protected benzo[b]furan 15 as a colorless oil.

Fuente