methyl 5-((tert-butyldimethylsilyloxy)(6-phenoxy-1,2,3,4-tetrahydronaphthalen-2-yl)methyl)-1,3,4-oxadiazole-2-carboxylate

Base Information

Chemical Name:methyl 5-((tert-butyldimethylsilyloxy)(6-phenoxy-1,2,3,4-tetrahydronaphthalen-2-yl)methyl)-1,3,4-oxadiazole-2-carboxylate
CAS No.:1289564-56-2
Molecular Formula:C₂₇H₃₄N₂O₅Si
Molecular Weight:494.663
Hs Code.:

Synonyms:methyl 5-((tert-butyldimethylsilyloxy)(6-phenoxy-1,2,3,4-tetrahydronaphthalen-2-yl)methyl)-1,3,4-oxadiazole-2-carboxylate

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Chemical Property of methyl 5-((tert-butyldimethylsilyloxy)(6-phenoxy-1,2,3,4-tetrahydronaphthalen-2-yl)methyl)-1,3,4-oxadiazole-2-carboxylate

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Technology Process of methyl 5-((tert-butyldimethylsilyloxy)(6-phenoxy-1,2,3,4-tetrahydronaphthalen-2-yl)methyl)-1,3,4-oxadiazole-2-carboxylate

There total 14 articles about methyl 5-((tert-butyldimethylsilyloxy)(6-phenoxy-1,2,3,4-tetrahydronaphthalen-2-yl)methyl)-1,3,4-oxadiazole-2-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 26.0%

: 1289564-54-0
methyl {N'-[2-(tert-butyldimethylsilyloxy)-2-(6-phenoxy-1,2,3,4-tetrahydronaphthalen-2-yl)acetyl]hydrazino}-2-oxo-acetate

: 1289564-56-2
methyl 5-((tert-butyldimethylsilyloxy)(6-phenoxy-1,2,3,4-tetrahydronaphthalen-2-yl)methyl)-1,3,4-oxadiazole-2-carboxylate

Guidance literature:: With triethylamine; p-toluenesulfonyl chloride; In dichloromethane; at 20 ℃; for 16h;
DOI:10.1021/jm101597x

Reference yield:

: 1289564-46-0
2-hydroxy-2-(6-phenoxy-1,2,3,4-tetrahydronaphthalen-2-yl)acetonitrile

: 1289564-56-2
methyl 5-((tert-butyldimethylsilyloxy)(6-phenoxy-1,2,3,4-tetrahydronaphthalen-2-yl)methyl)-1,3,4-oxadiazole-2-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: hydrogenchloride / ethyl acetate / 16 h / Reflux; Inert atmosphere

2: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C

3: water; lithium hydroxide / tetrahydrofuran; methanol / 16 h / 20 °C

4: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 16 h / 20 °C

5: triethylamine; p-toluenesulfonyl chloride / dichloromethane / 16 h / 20 °C

With 1H-imidazole; hydrogenchloride; water; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; p-toluenesulfonyl chloride; lithium hydroxide; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jm101597x

Reference yield:

: 1289564-48-2
methyl 2-hydroxy-2-(6-phenoxy-1,2,3,4-tetrahydronaphthalen-2-yl)acetate

: 1289564-56-2
methyl 5-((tert-butyldimethylsilyloxy)(6-phenoxy-1,2,3,4-tetrahydronaphthalen-2-yl)methyl)-1,3,4-oxadiazole-2-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C

2: water; lithium hydroxide / tetrahydrofuran; methanol / 16 h / 20 °C

3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 16 h / 20 °C

4: triethylamine; p-toluenesulfonyl chloride / dichloromethane / 16 h / 20 °C

With 1H-imidazole; water; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; p-toluenesulfonyl chloride; lithium hydroxide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm101597x