Reacción #65983

Ecuación de reacción

5-benzyloxytryptophol

diethyl ketone

p-toluene sulfonic acid

→

pure title compound

1,3,4,9-Tetrahydro-1,1-diethyl-6-(phenylmethoxy)pyrano[3,4-b]indole

Disolventes

benzene

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturais refluxed for 3.5 hours
2. 2
   Otroto remove the water
3. 3
   Lavadowashed with 5% sodium bicarbonate, water (200 mL), brine (200 mL)
4. 4
   Secadodried (MgSO4)
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated
7. 7
   Otroto give 9.9 g of crude product
8. 8
   Otrochromatographed on silica gel using 15% ethyl acetate/hexane as an eluent

Procedimiento

A mixture consisting of 5-benzyloxytryptophol (7.0 g, 0.0262 mol), diethyl ketone (10 mL), benzene (400 mL) and p-toluene sulfonic acid is refluxed for 3.5 hours using a Dean-Stark tap to remove the water. The reaction mixture is cooled to room temperature, washed with 5% sodium bicarbonate, water (200 mL), brine (200 mL), dried (MgSO4), filtered and concentrated to give 9.9 g of crude product. The crude product is flash chromatographed on silica gel using 15% ethyl acetate/hexane as an eluent to afford 6.5 g of pure title compound.

Fuente