Sodium Azide → 3-Azidomethyl-3-methyloxetane

HRID 259851Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 259851
Cl[CH2:2][C:3]1([CH3:7])[CH2:6][O:5][CH2:4]1.[N-:8]=[N+:9]=[N-:10].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[N:8]([CH2:2][C:3]1([CH3:7])[CH2:6][O:5][CH2:4]1)=[N+:9]=[N-:10]

Komponenten

5

Edukt 2

HCID 33557Sodium AzideHCID 791123-(Chloromethyl)-3-methyloxetane

Produkt 1

HCID 111477193-Azidomethyl-3-methyloxetaneAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 3-chloromethyl-3-methyloxetane (10.1 g, 83.5 mmol), tetra-n-butylammonium bromide (0.308 g, 0.96 mmol), sodium azide (6.5 g, 100 mmol) and water (27 mL) was heated at about 96° C. to about 103° C. for 4.5 h, after which time gas chromatographic analysis of the mixture indicated that the reaction had reached completion. The mixture was cooled to ambient temperature, and extracted with methylene chloride (25 mL). The organic extract was passed through a column containing aluminum oxide (10 g), and the column was rinsed with additional methylene chloride. The solvent was evaporated to give 9.84 g (93% yield) of 3-azidomethyl-3methyloxetane (>99.5% purity by glc and NMR analysis). NMR: 1H NMR: δ1.32 (s, 3H), 3.52 (s, 2H), 4.25 & 4.35 (AB, J=6.0 Hz, 4H); 13C NMR: δ21.44, 58.33, 40.03, 79.76; glc Rt= 3.19 min.

Aufarbeitung

  1. temperaturewas heated at about 96° C. to about 103° C. for 4.5 h
  2. extractionextracted with methylene chloride (25 mL)
  3. extractionThe organic extract
  4. additioncontaining aluminum oxide (10 g)
  5. washthe column was rinsed with additional methylene chloride
  6. customThe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-49ae46dc72e84376a7d655772ddf8277
Quelldatensatz
uspto-grants-1996_06
Patentnummer
US05523424

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