반응 #50880

반응 방정식

3-hydroxymethylbenzaldehyde

t-butylchlorodiphenyl silane

4-pyrrolidinopyridine

→

title compound

3-t-butyldiphenylsilyloxymethylbenzaldehyde

용매

methylene chloride

triethylamine

반응 조건

후처리

1. 1
   기타The solution was quenched with 25% ammonium acetate
2. 2
   추출extracted with ethyl acetate, which
3. 3
   세척was washed with brine (2×)
4. 4
   건조dried over sodium sulfate
5. 5
   여과filtered
6. 6
   기타evaporated to dryness
7. 7
   기타Purification by flash chromatography

실험 절차

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.

출처