反応 #974

反応方程式

4-phenyl-1-butanol

chlorochromate

PCC

→

aldehyde

収率 22.7%

4-Phenyl-1-butanal

収率 22.7%

溶媒

CH2Cl2

ether

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   ろ過filtered through celite
3. 3
   その他to give 2.5 g of the crude product
4. 4
   洗浄Flash chromatography (elution with 5% ethyl acetate in hexane)

実験手順

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.

出典