반응 #509457

반응 방정식

5-phenyl-2H-tetrazole

4-(pyridin-2-yl)but-3-yn-1-ol

triphenylphosphine

→

2-(4-(5-phenyl-2H-tetrazol-2-yl)but-1-ynyl)pyridine

수율 51.0%

용매

DCM

반응 조건

후처리

1. 1
   workup.ADDITIONwas added dropwise, at 0° C. over a period of 30 min The reaction mixture
2. 2
   온도was then warmed to room temperature
3. 3
   workup.STIRRINGstirred over night
4. 4
   여과The reaction mixture was filtered through celite
5. 5
   세척the cake was washed with DCM
6. 6
   세척The combined organic layers were washed with aqueous ammoniac, brine
7. 7
   건조dried over MgSO4
8. 8
   여과filtered
9. 9
   농축concentrated
10. 10
    기타The residue was purified by flash chromatography (prepacked 25 g silicagel column, DCM 100% as eluent)

실험 절차

A mixture of 5-phenyl-2H-tetrazole (330 mg, 2.2 mmol), 4-(pyridin-2-yl)but-3-yn-1-ol (220 mg, 1.49 mmol) and triphenylphosphine polymer supported (750 mg, 2.2 mmol, loading 3 mmol/g) were dissolved DCM (3 mL) and stirred at 0° C. Diisoprpylazodicarboxylate (452 mg, 2.2 mmol) was added dropwise, at 0° C. over a period of 30 min The reaction mixture was then warmed to room temperature and stirred over night. The reaction mixture was filtered through celite and the cake was washed with DCM. The combined organic layers were washed with aqueous ammoniac, brine, dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (prepacked 25 g silicagel column, DCM 100% as eluent) to afford 209 mg of 2-(4-(5-phenyl-2H-tetrazol-2-yl)but-1-ynyl)pyridine (Yield: 51%) as a pink powder (M.P.=71-73° C.).

출처