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

HRID 862395Notes

Reaction equation

HRID 862395 reaction equation
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]

Participants

5

Reactant 2

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

Product 1

HCID 67627134HCID 67627134, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 6344DichloromethaneSolvent

Procedure

(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%).

Workup

  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)

Sources & evidence

ORD record
ord-6c2c0a33a11a4aa4bc833b045bdf3143
Source dataset
uspto-grants-1998_02
Patent number
US05719139

Reaction notes

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