18-Crown-6 → HCID 14891674, compound
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
Product 1
Reagents, catalysts & solvents 1
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
- customAfter one hour the solution was partitioned between brine and ethylacetate
- customThe organic phase was separated
- dry with materialdried (Na2SO4)
- customevaporated
- customchromatographed on silica gel 60 (<230 mesh)
- washeluting with ethylacetate:hexane 6:4
- 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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