反応 #309152
ord-2fe2a5c6810a4b97933ac6b5f2bffc25
反応方程式
反応条件
後処理
- 1温度to slowly warm from −78° C. to rt over 15 hours
- 2抽出extracted with EtOAc
- 3乾燥dried over sodium sulfate
- 4ろ過filtered
- 5濃縮concentrated
- 6その他The crude residue was purified by column chromatography
- 7洗浄eluting with 1-20% EtOAc/Hexane
- 8その他the solvent removed in vacuo
実験手順
To a solution of ethyl (4-bromophenyl)acetate (143 g, 588 mmol) in THF (800 mL) was added LHMDS (1.13 eq in THF) at −78° C. After 30 minutes, the reaction mixture was added to a solution of 3-chloro-2-chloromethyl-1-propene (147 g, 1180 mmol) in THF (500 mL) at −78° C. via cannula. The reaction was allowed to slowly warm from −78° C. to rt over 15 hours. The reaction mixture was poured into sodium bicarbonate, extracted with EtOAc, dried over sodium sulfate, filtered and concentrated. The crude residue was purified by column chromatography eluting with 1-20% EtOAc/Hexane. The appropriate fractions were combined and the solvent removed in vacuo to give ethyl 2-(4-bromophenyl)-4-(chloromethyl)pent-4-enoate (1-1) as a clear oil. MS (M+H)+: 332.