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ChemicalBook CAS DataBase List (4-tert-butyl-1H-iMidazol-5-yl)Methanol
51721-22-3

(4-tert-butyl-1H-iMidazol-5-yl)Methanol synthesis

5synthesis methods
-

Yield: 95%

Reaction Conditions:

with lithium aluminium tetrahydride in tetrahydrofuran at 0 - 20;Inert atmosphere;

Steps:

4.2.6 Preparation of (5-(tert-butyl)-1H-imidazol-4-yl) methanol (9a)
Ethyl 5-(tert-butyl)-1H-imidazole-4-carboxylate (9.92g, 261.28mmol) in THF (80ml) was added dropwise to a solution of LiAlH4 (17.07g, 87.09mol) in THF (80ml) at 0°C under nitrogen. The mixture was stirred for 4h at room temperature. To this solution, water was added and the resulting precipitate was removed by celite filtration. The filtrate was evaporated in vacuo to produce 15.36g of white solid with a yield of 95%. The crude product was used in the next step without further purification. MS (ESI) m/z: [M+H]+ Calcd for C8H15N2O: 155.12, Found: 154.64.

References:

Ding, Zhongpeng;Li, Feifei;Li, Feng;Li, Wenbao;Liu, Yuqian;Wang, Shixiao;Zhao, Jianchun;Zhong, Changjiang [Bioorganic and medicinal chemistry,2020]