Reaktionsgleichung
BrCC1(CO)COC1.[N:9]([CH2:12][C:13]1([CH2:17][OH:18])[CH2:16][O:15][CH2:14]1)=[N+:10]=[N-:11].[N-]=[N+]=[N-].[Na+].ClCC1(CO[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)COC1.ClCC1(C)COC1>CC(C)=O.O>[N:9]([CH2:12][C:13]1([CH2:17][O:18][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:16][O:15][CH2:14]1)=[N+:10]=[N-:11]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
As such, it has been discovered that monofunctional azidooxetane compounds, i.e., 3-azidomethyl-3-R1 -oxetanes, can also be prepared by combining a neat halooxetane with an aqueous metallic azide solution and a phase transfer catalyst (PTC). For example, using the process of the present invention, 3-chloromethyl-3-methyloxetane gives the corresponding 3-azidomethyl-3-methyloxetane (AMMO) in 97% yield. Moreover, 3-bromomethyl-3-hydroxymethyloxetane was previously converted to the corresponding 3-azidomethyl-3-hydroxymethyloxetane in acetone. Using the process of the present invention, however, 3-bromomethyl-3-hydroxymethyloxetane is converted to the corresponding 3-azidomethyl-3-hydroxymethyloxetane, without the use of an organic solvent, using an aqueous sodium azide solution and a phase transfer catalyst. The process of the present invention gives the same result with a faster rate of reaction and without the use of an organic solvent. In addition, 3-chloromethyl-3-methyloxetane 3-chloromethyl-3-phenoxymethyloxetane reacts with an aqueous solution of sodium azide in water with a PTC to give 3-azidomethyl-3-phenoxymethyloxetane in 87% yield.
Aufarbeitung
- customThe process of the present invention gives the
- customsame result with a faster rate of reaction and without the use of an organic solvent
Quellen und Nachweise
- ORD-Eintrag
- ord-7f3adcefb4774a9fb881adc0618bb4e7
- Quelldatensatz
- uspto-grants-1996_06
- Patentnummer
- US05523424
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