Reaktion #485194

Reaktionsgleichung

HCl

sodium azide

sodium bicarbonate

alcohol

4-(3-{[tert-butyl(diphenyl)silyl]oxy}phenyl)but-3-yn-1-ol

diphenylphosphoryl azide

DBU

→

title compound

[3-(4-azidobut-1-ynyl)phenoxy](tert-butyl)diphenylsilane

Lösungsmittel

DMF

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ethyl acetate (3×20 mL)
2. 2
   TrocknenThe combined organic layers were dried over sodium sulfate
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated in vacuo
5. 5
   Sonstigeto provide a brown oil
6. 6
   Extraktionextracted with methylene chloride (3×50 mL)
7. 7
   TrocknenThe combined organic layers were dried over sodium sulfate
8. 8
   Filtrationfiltered
9. 9
   Einengenconcentrated in vacuo
10. 10
    SonstigeThe crude product was purified by column chromatography (0→20% ethyl acetate/hexane)

Vorschrift

To a solution of alcohol from Step B (375 mg, 0.936 mmol) and diphenylphosphoryl azide (0.242 mL, 1.12 mmol) in toluene (3 mL) at 0° C. was added DBU (0.154 mL, 1.03 mmol). The reaction mixture was stirred at 25° C. for 16 hours, then poured onto 10% HCl (20 mL) and extracted with ethyl acetate (3×20 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to provide a brown oil. A solution of the oil and sodium azide (66.9 mg, 1.03 mmol) in DMF (3 mL) was heated to 85° C. for 16 hours. The reaction mixture was poured onto saturated sodium bicarbonate (50 mL) and extracted with methylene chloride (3×50 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. The crude product was purified by column chromatography (0→20% ethyl acetate/hexane) to provide the title compound.

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