反応 #985

反応方程式

ester

4-[3-[1,3]-Dioxolan-2-yl-propyl)benzoic acid methyl ester

diisobutylaluminum hydride

→

alcohol

収率 95.8%

[4-(3-[1,3]-Dioxan-2-yl-propyl)phenyl]methanol

収率 95.8%

溶媒

THF

反応条件

後処理

1. 1
   その他The reaction was quenched with saturated potassium sodium tartrate
2. 2
   抽出extracted three times with ethyl acetate
3. 3
   乾燥The combined organic extracts were dried over MgSO4
4. 4
   ろ過filtered
5. 5
   濃縮concentrated

実験手順

To a solution of 2.85 g (11.4 mmol) of ester 169 in 25 mL of THF at 0° C. was added 4.4 mL (24.7 mmol) of diisobutylaluminum hydride and the resulting mixture was allowed to stir at 0° C. for 15 min. The reaction was quenched with saturated potassium sodium tartrate and extracted three times with ethyl acetate. The combined organic extracts were dried over MgSO4, filtered and concentrated to yield 2.58 g of the crude alcohol 170 as an oil. 1H NMR consistent with the product.

出典