Reacción #50880

Ecuación de reacción

3-hydroxymethylbenzaldehyde

t-butylchlorodiphenyl silane

4-pyrrolidinopyridine

→

title compound

3-t-butyldiphenylsilyloxymethylbenzaldehyde

Disolventes

methylene chloride

triethylamine

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe solution was quenched with 25% ammonium acetate
2. 2
   Extracciónextracted with ethyl acetate, which
3. 3
   Lavadowas washed with brine (2×)
4. 4
   Secadodried over sodium sulfate
5. 5
   Filtraciónfiltered
6. 6
   Otroevaporated to dryness
7. 7
   OtroPurification by flash chromatography

Procedimiento

To a solution of 3-hydroxymethylbenzaldehyde (step 1) (3 g) in methylene chloride (15 mL) and triethylamine (4.1 mL) was slowly added t-butylchlorodiphenyl silane (8 mL). Finally, a few mgs of 4-pyrrolidinopyridine was added as a catalyst. The reaction mixture was stirred overnight at room temperature (R.T.). The solution was quenched with 25% ammonium acetate and extracted with ethyl acetate, which was washed with brine (2×), dried over sodium sulfate, filtered and evaporated to dryness. Purification by flash chromatography, using 4% ethyl acetate in hexane afforded the title compound.

Fuente