Triethylamine → 1-[tert-Butyl(dimethyl)silyl]-4-(prop-2-en-1-yl)azetidin-2-one

HRID 543560Notes

Reaction equation

HRID 543560 reaction equation
C([N:4]1[CH2:7][CH2:6][C:5]1=[O:8])C=C.[Si:9](Cl)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].C(N([CH2:22][CH3:23])CC)C.[CH2:24](OC(=O)C)C.O>CN(C)C=O>[CH2:24]([CH:7]1[N:4]([Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])[C:5](=[O:8])[CH2:6]1)[CH:22]=[CH2:23]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 12376723HCID 12376723, compoundHCID 22728543Water ethylacetate

Product 1

HCID 128821041-[tert-Butyl(dimethyl)silyl]-4-(prop-2-en-1-yl)azetidin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Allylazetidinone (0.22 g) was dissolved in dry N,N-dimethylformamide (5 ml) containing t-butyldimethylsilyl chloride (0.33 g). The solution was cooled to 0° and was treated with triethylamine (0.22 g) in N,N-dimethylformamide (1 ml) over a period of 15 minutes. After a further 15 minutes the solution was poured into ethylacetate/water. The organic phase was separated, washed with dil HCl, brine, dried (Na2SO4), evaporated, and chromatographed on silica gel 60 (230 mesh) eluting with ethylacetate. This gave 4-allyl-1-t-butyldimethylsilylazetidin-2-one (0.39 g).

Workup

  1. temperatureThe solution was cooled to 0°
  2. customThe organic phase was separated
  3. washwashed with dil HCl, brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customchromatographed on silica gel 60 (230 mesh)
  7. washeluting with ethylacetate

Sources & evidence

ORD record
ord-097052cf6dbe476c9929959513933e1f
Source dataset
uspto-grants-1984_05
Patent number
US04446146

Reaction notes

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