反応 #421095

反応方程式

3-(4-Methoxy-phenyl)-propionic acid

DIBAL-H

NH4Cl

→

3-(4-methoxy-phenyl)-propionaldehyde

収率 70.7%

溶媒

toluene

dry ice acetone

反応条件

後処理

1. 1
   抽出The solution was extracted twice with ether
2. 2
   洗浄the organic layer was washed with brine
3. 3
   乾燥dried over MgSO4(s)
4. 4
   濃縮concentrated under reduced pressure
5. 5
   その他The residue was purified by column chromatography on silica gel

実験手順

3-(4-Methoxy-phenyl)-propionic acid (9a, 1.80 g, 10.0 mmol) in toluene (25.0 mL) was cooled to −78° C. in dry ice-acetone bath for 5-10 minutes under N2. DIBAL-H (11.0 mmol) was slowly added by syringe and stirred for 2 hours at −78° C. Then, the reaction mixture was poured quickly into an aqueous NH4Cl solution with vigorous stirring. The solution was extracted twice with ether and the organic layer was washed with brine, dried over MgSO4(s), and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to provide 3-(4-methoxy-phenyl)-propionaldehyde (9b, 1.16 g, 7.07 mmol) as yellow oil in 70.7% yield.

出典