반응 #309152
ord-2fe2a5c6810a4b97933ac6b5f2bffc25
반응 방정식
반응 조건
후처리
- 1온도to slowly warm from −78° C. to rt over 15 hours
- 2추출extracted with EtOAc
- 3건조dried over sodium sulfate
- 4여과filtered
- 5농축concentrated
- 6기타The crude residue was purified by column chromatography
- 7세척eluting with 1-20% EtOAc/Hexane
- 8기타the solvent removed in vacuo
실험 절차
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.