تفاعل #65324

معادلة التفاعل

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

sodium azide

azide

→

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

المذيبات

dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   استخلاصThe reaction mixture was transferred to a 11 extraction funnel
2. 2
   استخلاصThe aqueous phase was extracted with ethyl acetate (80 ml)
3. 3
   غسيلthe combined organic phases were washed with water (2×120 ml)
4. 4
   تجفيفdried over magnesium sulphate
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated in vacuo to a pale brown oil
7. 7
   أخرىCrystallisation
8. 8
   workup.ADDITIONby adding ether (7 ml)
9. 9
   أخرىCrystals were collected on a glass sinter
10. 10
    غسيلwashed with cold ether
11. 11
    أخرىdried under vacuum for 28 hours
12. 12
    تركيزThe mother liquors were concentrated
13. 13
    workup.ADDITIONdiluted with ether
14. 14
    أخرىyielding another 1 g

الإجراء التجريبي

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.

المصدر