18-Crown-6 → HCID 14891674, compound

HRID 543562Notes

Reaction equation

HRID 543562 reaction equation
[CH2:1]([CH:4]1[N:7]([Si](C(C)(C)C)(C)C)[C:6](=[O:15])[CH:5]1[CH3:16])[CH:2]=[CH2:3].[F-].[K+].C1OCCOCCOCCOCCOCCOC1>O1CCCC1>[CH2:1]([CH:4]1[NH:7][C:6](=[O:15])[CH:5]1[CH3:16])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 2855718-Crown-6HCID 522689Potassium FluorideHCID 20461605HCID 20461605, compound

Product 1

HCID 14891674HCID 14891674, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Part of the isomeric mixture from (ii) (1.20 g) in dry tetrahydrofuran (50 ml) was treated with potassium fluoride (0.45 g) and 18-crown-6 ether (0.07 g). After one hour the solution was partitioned between brine and ethylacetate. The organic phase was separated, dried (Na2SO4), evaporated and chromatographed on silica gel 60 (<230 mesh) eluting with ethylacetate:hexane 6:4. This separated the trans and cis isomers of 4-allyl-3-methyl azetidin-2-one.

Workup

  1. customAfter one hour the solution was partitioned between brine and ethylacetate
  2. customThe organic phase was separated
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customchromatographed on silica gel 60 (<230 mesh)
  6. washeluting with ethylacetate:hexane 6:4
  7. customThis separated the trans

Sources & evidence

ORD record
ord-9486123c9a724820aea2bc4bbe6823ab
Source dataset
uspto-grants-1984_05
Patent number
US04446146

Reaction notes

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