반응 #974

반응 방정식

4-phenyl-1-butanol

chlorochromate

PCC

→

aldehyde

수율 22.7%

4-Phenyl-1-butanal

수율 22.7%

용매

CH2Cl2

ether

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   여과filtered through celite
3. 3
   기타to give 2.5 g of the crude product
4. 4
   세척Flash chromatography (elution with 5% ethyl acetate in hexane)

실험 절차

To a solution of 3.2 mL (20.8 mmol) of 4-phenyl-1-butanol (Aldrich Chemical Co.) in 20 mL of CH2Cl2 at 0° C. was added 3.2 g of powdered 3 Å molecular sieves and then 5.37 g (24.9 mmol) of pyridinum chlorochromate (PCC). The resulting suspension was stirred at 0° C. for 1 h at which time an additional 2.16 g (10.0 mmol) of PCC was added and the reaction mixture was warmed to room temperature. After stirring at ambient temperature for 0.5 h, the reaction mixture was diluted with ether and filtered through celite to give 2.5 g of the crude product. Flash chromatography (elution with 5% ethyl acetate in hexane) yielded 700 mg of the aldehyde 119. 1H NMR was consistent with the structure.

출처