反応 #489024

反応方程式

(E)-but-2-enoyl chloride

nBuLi

hexane

(S)-4-Benzyloxazolidin-2-one

THF

→

desired product

収率 79.0%

(1S,2S,4S)-2,4-dimethylcyclohexanecarboxylic acid

収率 79.0%

反応条件

後処理

1. 1
   その他The cold bath was removed
2. 2
   workup.STIRRINGto stir at room temperature for 1 h, whereupon saturated NH4Cl solution (200 mL)
3. 3
   workup.ADDITIONwas added
4. 4
   その他Most of the THF was removed under vacuum
5. 5
   その他the mixture was partitioned between ether and brine
6. 6
   乾燥After drying over Na2SO4
7. 7
   濃縮the organic layer was concentrated
8. 8
   その他the residue purified by silica gel chromatography (20% EtOAc in hexanes)

実験手順

(S)-4-Benzyloxazolidin-2-one (35 g, 0.2 mol) was dissolved in THF (500 mL) and cooled to −78° C. A solution of nBuLi in hexane (80 mL, 0.2 mol) was added dropwise. The solution was stirred at this temperature for 30 min and then (E)-but-2-enoyl chloride (19 mL, 0.2 mol) was added slowly. The cold bath was removed and the reaction was allowed to stir at room temperature for 1 h, whereupon saturated NH4Cl solution (200 mL) was added. Most of the THF was removed under vacuum and the mixture was partitioned between ether and brine. After drying over Na2SO4, the organic layer was concentrated and the residue purified by silica gel chromatography (20% EtOAc in hexanes) to give the desired product (39 g, 79% yield) as a white solid.

出典