toluene-4-sulfonic acid 2-(1-but-3-enyl-1-ethynyl-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-ethyl ester

Base Information

• Chemical Name: toluene-4-sulfonic acid 2-(1-but-3-enyl-1-ethynyl-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-ethyl ester
• CAS No.: 1258305-90-6
• Molecular Formula: C₂₆H₃₁NO₅S
• Molecular Weight: 469.602

Synonyms:toluene-4-sulfonic acid 2-(1-but-3-enyl-1-ethynyl-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-ethyl ester

Chemical Property of toluene-4-sulfonic acid 2-(1-but-3-enyl-1-ethynyl-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-ethyl ester

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Technology Process of toluene-4-sulfonic acid 2-(1-but-3-enyl-1-ethynyl-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-ethyl ester

There total 7 articles about toluene-4-sulfonic acid 2-(1-but-3-enyl-1-ethynyl-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-ethyl ester 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: 22.0%

2-(1-but-3-enyl-1-ethynyl-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-ethanol (1258305-87-1) + p-toluenesulfonylanhydride (4124-41-8) → toluene-4-sulfonic acid 2-(1-but-3-enyl-1-ethynyl-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-ethyl ester (1258305-90-6)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/ol102535u

Reference yield:

pent-4-enoyl chloride (39716-58-0) → toluene-4-sulfonic acid 2-(1-but-3-enyl-1-ethynyl-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-ethyl ester (1258305-90-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

2.1: trichlorophosphate / acetonitrile / 1.5 h / 95 °C / Inert atmosphere

2.2: 0 °C / pH 9 - 10

3.1: acetonitrile / 24 h / 85 °C / Inert atmosphere

4.1: tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

5.2: Saturated solution; solid phase reaction

6.1: dmap; triethylamine / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

With dmap; tetrabutyl ammonium fluoride; triethylamine; trichlorophosphate; In tetrahydrofuran; dichloromethane; acetonitrile; 2.1: Bischler-Napieralski reaction / 4.1: Grignard reaction;

DOI:10.1021/ol102535u

Reference yield:

2-(3,4-dimethoxyphenyl)-ethylamine (120-20-7) → toluene-4-sulfonic acid 2-(1-but-3-enyl-1-ethynyl-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-ethyl ester (1258305-90-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

2.1: trichlorophosphate / acetonitrile / 1.5 h / 95 °C / Inert atmosphere

2.2: 0 °C / pH 9 - 10

3.1: acetonitrile / 24 h / 85 °C / Inert atmosphere

4.1: tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

5.2: Saturated solution; solid phase reaction

6.1: dmap; triethylamine / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

With dmap; tetrabutyl ammonium fluoride; triethylamine; trichlorophosphate; In tetrahydrofuran; dichloromethane; acetonitrile; 2.1: Bischler-Napieralski reaction / 4.1: Grignard reaction;

DOI:10.1021/ol102535u

upstream raw materials:

1-(but-3-enyl)-2-(2-(tert-butyldiphenylsilyloxy)ethyl)-1-ethynyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

2-(1-but-3-enyl-1-ethynyl-6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-ethanol

p-toluenesulfonylanhydride

pent-4-enoyl chloride

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