Tetrahydrofuran → (S)-4-isopropyl-3-(4-pentenoyl)-oxazolidin-2-one

HRID 2399893

반응식

HRID 2399893 반응식
[CH3:1][CH:2]([CH:4]1[CH2:8][O:7][C:6](=[O:9])[NH:5]1)[CH3:3].C([Li])CCC.[CH2:15](Cl)[CH2:16][CH2:17][CH:18]=[CH2:19].[O:21]1CCCC1>CCCCCC.[Cl-].[NH4+].C(OCC)C>[CH3:1][CH:2]([C@H:4]1[CH2:8][O:7][C:6](=[O:9])[N:5]1[C:15](=[O:21])[CH2:16][CH2:17][CH:18]=[CH2:19])[CH3:3]

참가 물질

8

반응물 4

HCID 8028Tetrahydrofuran2회HCID 5193532-Oxazolidinone, 4-(1-methylethyl)-HCID 5230425-Chloro-1-penteneHCID 178418339Butyllithium

생성물 1

HCID 11820460(S)-4-isopropyl-3-(4-pentenoyl)-oxazolidin-2-one

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 8058Hexane용매HCID 25517Ammonium Chloride용매

실험 절차

To a -78° C. solution of 5.0 g of 4-(1-methylethyl)-2-oxazolidinone in 80 ml of tetrahydrofuran is added, dropwise, 15.5 ml of 2.5M n-butyl lithium in hexane. After stirring for 30 minutes, a solution of 4.8 g of 4-pentenyl chloride in 30 ml of tetrahydrofuran is added, dropwise, and the resulting solution is stirred at -78° C. for 3.5 hours. The reaction is diluted with aqueous ammonium chloride and diethyl ether. The organic layer is washed with water, dried and concentrated in vacuo. The residue is purified by chromatography (silica gel, 25% ethyl acetate/petroleum ether) to give 5.8 g of the desired product as a pale yellow oil.

후처리

  1. stirringdropwise, and the resulting solution is stirred at -78° C. for 3.5 hours
  2. washThe organic layer is washed with water
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by chromatography (silica gel, 25% ethyl acetate/petroleum ether)

출처 및 근거

ORD 기록
ord-5fc9f1701d944457b40192659c8f3fa2
출처 데이터셋
uspto-grants-1995_09
특허 번호
US05451685

연결된 노트

불러오는 중…