Reaktion #65324

Reaktionsgleichung

2-Benzyloxymethyl-2-(trifluoromethylsulfonyloxy)-1-phthalimido-ethane

sodium azide

azide

→

2-Benzyloxymethyl-2-azido-1-phthalimido-ethane

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThe reaction mixture was transferred to a 11 extraction funnel
2. 2
   ExtraktionThe aqueous phase was extracted with ethyl acetate (80 ml)
3. 3
   Waschenthe combined organic phases were washed with water (2×120 ml)
4. 4
   Trocknendried over magnesium sulphate
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated in vacuo to a pale brown oil
7. 7
   SonstigeCrystallisation
8. 8
   workup.ADDITIONby adding ether (7 ml)
9. 9
   SonstigeCrystals were collected on a glass sinter
10. 10
    Waschenwashed with cold ether
11. 11
    Sonstigedried under vacuum for 28 hours
12. 12
    EinengenThe mother liquors were concentrated
13. 13
    workup.ADDITIONdiluted with ether
14. 14
    Sonstigeyielding another 1 g

Vorschrift

2-Benzyloxymethyl-2-(trifluoromethylsulfonyloxy)-1-phthalimido-ethane (8.5 g, 19.1 mmol) and sodium azide (2.5 g, 38.2 mmol) were stirred in dimethylformamide (80 ml) at 60° C. for 6 hours Under nitrogen. TLC in several systems was inconclusive because the Rf of the product was identical to the Rf of the starting material. A small sample was worked up and IR indicated full conversion to the azide. The reaction mixture was transferred to a 11 extraction funnel and distributed between ethyl acetate (350 ml) and water (130 ml). The aqueous phase was extracted with ethyl acetate (80 ml); the combined organic phases were washed with water (2×120 ml), dried over magnesium sulphate, filtered and concentrated in vacuo to a pale brown oil. Crystallisation was initiated by adding ether (7 ml). Crystals were collected on a glass sinter, washed with cold ether and dried under vacuum for 28 hours. Yield: 4.5 g (70%). The mother liquors were concentrated, diluted with ether and seeded with crystals from the first crop--yielding another 1 g. Total yield: 5.5 g (85%). The structure was confirmed by NMR and IR.

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