4-methoxy-2-methyl-3-(3-butenyl)pyridine

Base Information

Chemical Name:4-methoxy-2-methyl-3-(3-butenyl)pyridine
CAS No.:211758-56-4
Molecular Formula:C₁₁H₁₅NO
Molecular Weight:177.246
Hs Code.:

Synonyms:4-methoxy-2-methyl-3-(3-butenyl)pyridine

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Chemical Property of 4-methoxy-2-methyl-3-(3-butenyl)pyridine

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Technology Process of 4-methoxy-2-methyl-3-(3-butenyl)pyridine

There total 1 articles about 4-methoxy-2-methyl-3-(3-butenyl)pyridine 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:

: 5470-66-6
2-methyl-4-nitropyridine N-oxide

: 211758-56-4
4-methoxy-2-methyl-3-(3-butenyl)pyridine

Guidance literature:: Multi-step reaction with 5 steps

1: 84 percent / PCl₃ / CHCl₃ / 40 h / Ambient temperature

2: 50 percent / NaOH / dimethylsulfoxide / 0.5 h / 15 - 20 °C

3: 83 percent / methanol / Ambient temperature

4: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1 h, then -78 to 0 deg C, 45 min, 2.) THF, hexane, 1.25 h

5: 94 percent / Na/Hg, Na₂HPO₄ / methanol / 2.5 h / Ambient temperature

With sodium hydroxide; disodium hydrogenphosphate; sodium amalgam; n-butyllithium; phosphorus trichloride; In methanol; chloroform; dimethyl sulfoxide;
DOI:10.1021/jo9801770

Reference yield:

: 211758-56-4
4-methoxy-2-methyl-3-(3-butenyl)pyridine

: 211758-69-9
(4E,16E)-7-Benzenesulfonyl-12,24-dimethoxy-9,21-diaza-tricyclo[18.4.0.0^8,13]tetracosa-1⁽²⁴⁾,4,8,10,12,16,20,22-octaene

Guidance literature:: Multi-step reaction with 11 steps

1: 89 percent / OsO₄, NaIO₄ / tetrahydrofuran / 7 h / 0 - 20 °C

2: 81 percent / tetrahydrofuran / 4.5 h / -50 - 20 °C

3: 95 percent / Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 6.5 h / Ambient temperature

4: 97 percent / m-CPBA / CH₂Cl₂ / 3 h / Ambient temperature

5: 1.) p-TsCl, Et₃N / 1.) CH₂Cl₂, -50 deg C, 5 h, 2.) DMF, room temp., 12 h

6: 1.) NaHMDS, 2.) Pd₂(dba)3*CHCl₃, 1,2-bis(diphenylphosphino)ethane / 1.) THF, -78 deg C, 70 min, 2.) THF, reflux, 4 h

7: 66 percent / Na/Hg, Na₂HPO₄ / methanol / 2 h / Ambient temperature

8: 100 percent / n-Bu₄NF / tetrahydrofuran / 5.5 h / 0 °C

9: 98 percent / Et₃N, 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 50 h / Ambient temperature

10: 78 percent / tetra-n-butylammonium peroxymonosulfate / CH₂Cl₂ / 24 h / Ambient temperature

11: 1.) NaHMDS, 2.) Pd₂(dba)3*CHCl₃, 1,2-bis(diphenylphosphino)ethane / 1.) THF, -78 deg C, 30 min, 2.) THF, reflux, 7 h

With dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium periodate; disodium hydrogenphosphate; sodium amalgam; osmium(VIII) oxide; tetra-n-butylammonium peroxomonosulfate; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; triethylamine; p-toluenesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; 1,2-bis-(diphenylphosphino)ethane; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo9801770

Reference yield:

: 211758-56-4
4-methoxy-2-methyl-3-(3-butenyl)pyridine

: 211758-66-6
5-{4-Methoxy-2-[(E)-6-(4-methoxy-2-phenylsulfanylmethyl-pyridin-3-yl)-hex-3-enyl]-pyridin-3-yl}-pent-1-en-3-ol

Guidance literature:: Multi-step reaction with 8 steps

1: 89 percent / OsO₄, NaIO₄ / tetrahydrofuran / 7 h / 0 - 20 °C

2: 81 percent / tetrahydrofuran / 4.5 h / -50 - 20 °C

3: 95 percent / Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 6.5 h / Ambient temperature

4: 97 percent / m-CPBA / CH₂Cl₂ / 3 h / Ambient temperature

5: 1.) p-TsCl, Et₃N / 1.) CH₂Cl₂, -50 deg C, 5 h, 2.) DMF, room temp., 12 h

6: 1.) NaHMDS, 2.) Pd₂(dba)3*CHCl₃, 1,2-bis(diphenylphosphino)ethane / 1.) THF, -78 deg C, 70 min, 2.) THF, reflux, 4 h

7: 66 percent / Na/Hg, Na₂HPO₄ / methanol / 2 h / Ambient temperature

8: 100 percent / n-Bu₄NF / tetrahydrofuran / 5.5 h / 0 °C

With dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium periodate; disodium hydrogenphosphate; sodium amalgam; osmium(VIII) oxide; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; triethylamine; p-toluenesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; 1,2-bis-(diphenylphosphino)ethane; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo9801770