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

HRID 1079024

반응식

HRID 1079024 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. [α]D26 =+79° (methylene chloride).

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-883850b5833e4156a9217c614cda6f9f
출처 데이터셋
uspto-grants-1996_08
특허 번호
US05550257

연결된 노트

불러오는 중…