1-Methoxy-3-trimethylsilyloxy-1,3-butadiene → HCID 67627134, 화합물

HRID 862395

반응식

HRID 862395 반응식
C(O[C@H:5]1[NH:8][C:7](=[O:9])[C@@H:6]1[C@H:10]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH3:11])(=O)C.[CH3:20][O:21][CH:22]=[CH:23][C:24]([O:26][Si](C)(C)C)=[CH2:25]>ClCCl.[I-].[Zn+2].[I-]>[Si:13]([O:12][C@@H:10]([C@@H:6]1[C@@H:5]([CH2:25][C:24](=[O:26])[CH:23]=[CH:22][O:21][CH3:20])[NH:8][C:7]1=[O:9])[CH3:11])([C:16]([CH3:17])([CH3:18])[CH3:19])([CH3:14])[CH3:15]

참가 물질

5

반응물 2

HCID 1010511-Methoxy-3-trimethylsilyloxy-1,3-butadieneHCID 10935078Azetidon

생성물 1

HCID 67627134HCID 67627134, 화합물수율 43%

시약·촉매·용매 2

HCID 9883512zinc(II)iodide촉매HCID 6344Dichloromethane용매

실험 절차

(3R,4R) 4-acetoxy-3-[(1R)-(1-(tert-butyldimethylsilyloxy)ethyl)]azetidin-2-one (2 g, 56.96 mM) was dissolved in dichloromethane (150 ml) at ambient temperature and 4-methoxy-2-trimethylsilyloxybut-1,3-diene (1.5 ml, 7.65 mM) added followed by zinc iodide (2.2 g, 17 mM). The reaction mixture was shielded from light and stirred for 15 hours. The mixture was then washed with a 5% aqueous solution of sodium bicarbonate (30 ml) and then water (30 ml). The organic phase was dried with magnesium sulphate and the solvent evaporated. The residue was purified by chromatography on silica, eluting with ethyl acetate/dichloromethane (1:1) to give (3S,4R) 3-((1R)-1-(tert-butyldimethylsilyloxy)ethyl)-4-(4-methoxy-2-oxobut-3-en-1-yl)azetidin-2-one (0.96 g, 43%).

후처리

  1. washThe mixture was then washed with a 5% aqueous solution of sodium bicarbonate (30 ml)
  2. dry with materialThe organic phase was dried with magnesium sulphate
  3. customthe solvent evaporated
  4. customThe residue was purified by chromatography on silica
  5. washeluting with ethyl acetate/dichloromethane (1:1)

출처 및 근거

ORD 기록
ord-6c2c0a33a11a4aa4bc833b045bdf3143
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05719139

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