methyl 5-(6-phenoxy-1,2,3,4-tetrahydronaphthalene-2-carbonyl)-[1,3,4]oxadiazole-2-carboxylate

Base Information

Chemical Name:methyl 5-(6-phenoxy-1,2,3,4-tetrahydronaphthalene-2-carbonyl)-[1,3,4]oxadiazole-2-carboxylate
CAS No.:1289561-17-6
Molecular Formula:C₂₁H₁₈N₂O₅
Molecular Weight:378.384
Hs Code.:

Synonyms:methyl 5-(6-phenoxy-1,2,3,4-tetrahydronaphthalene-2-carbonyl)-[1,3,4]oxadiazole-2-carboxylate

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Chemical Property of methyl 5-(6-phenoxy-1,2,3,4-tetrahydronaphthalene-2-carbonyl)-[1,3,4]oxadiazole-2-carboxylate

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Technology Process of methyl 5-(6-phenoxy-1,2,3,4-tetrahydronaphthalene-2-carbonyl)-[1,3,4]oxadiazole-2-carboxylate

There total 16 articles about methyl 5-(6-phenoxy-1,2,3,4-tetrahydronaphthalene-2-carbonyl)-[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: 75.0%

: 1289564-60-8
methyl 5-[hydroxy-(6-phenoxy-1,2,3,4-tetrahydronaphthalen-2-yl)methyl]-[1,3,4]oxadiazole-2-carboxylate

: 1289561-17-6
methyl 5-(6-phenoxy-1,2,3,4-tetrahydronaphthalene-2-carbonyl)-[1,3,4]oxadiazole-2-carboxylate

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1021/jm101597x

Reference yield:

: 65844-44-2
methyl 6-hydroxy-1,2,3,4-tetrahydronaphthalene-2-carboxylate

: 1289561-17-6
methyl 5-(6-phenoxy-1,2,3,4-tetrahydronaphthalene-2-carbonyl)-[1,3,4]oxadiazole-2-carboxylate

Guidance literature:: Multi-step reaction with 11 steps

1.1: copper diacetate / dichloromethane / 0.25 h / 20 °C / Molecular sieve

1.2: 17 h / 20 °C / Inert atmosphere

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C

3.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C

4.1: tetrahydrofuran; water / 16 h / 20 °C

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

6.1: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C

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

8.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 16 h / 20 °C

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

10.1: tris(dimethylamino)sulfonium trimethylsilyldifluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

11.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C

With 1H-imidazole; hydrogenchloride; lithium aluminium tetrahydride; tris(dimethylamino)sulfonium trimethylsilyldifluoride; water; copper diacetate; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; p-toluenesulfonyl chloride; lithium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; 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

: 1289561-17-6
methyl 5-(6-phenoxy-1,2,3,4-tetrahydronaphthalene-2-carbonyl)-[1,3,4]oxadiazole-2-carboxylate

Guidance literature:: Multi-step reaction with 6 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

5: tris(dimethylamino)sulfonium trimethylsilyldifluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

6: Dess-Martin periodane / dichloromethane / 2 h / 20 °C

With 1H-imidazole; tris(dimethylamino)sulfonium trimethylsilyldifluoride; water; Dess-Martin periodane; 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