ethyl 5-methyl-3-{[4-(tert-butyldiphenylsilyloxy)methyl]-1-(4-toluenesulfonyl)indol-3-yl}hex-4-enoate

Base Information

Chemical Name:ethyl 5-methyl-3-{[4-(tert-butyldiphenylsilyloxy)methyl]-1-(4-toluenesulfonyl)indol-3-yl}hex-4-enoate
CAS No.:862297-62-9
Molecular Formula:C₄₁H₄₇NO₅SSi
Molecular Weight:693.979
Hs Code.:

Synonyms:ethyl 5-methyl-3-{[4-(tert-butyldiphenylsilyloxy)methyl]-1-(4-toluenesulfonyl)indol-3-yl}hex-4-enoate

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Chemical Property of ethyl 5-methyl-3-{[4-(tert-butyldiphenylsilyloxy)methyl]-1-(4-toluenesulfonyl)indol-3-yl}hex-4-enoate

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Technology Process of ethyl 5-methyl-3-{[4-(tert-butyldiphenylsilyloxy)methyl]-1-(4-toluenesulfonyl)indol-3-yl}hex-4-enoate

There total 10 articles about ethyl 5-methyl-3-{[4-(tert-butyldiphenylsilyloxy)methyl]-1-(4-toluenesulfonyl)indol-3-yl}hex-4-enoate 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: 53.0%

: ethyl (E)-3-{4-[(tert-butyldiphenylsilyloxy)methyl]-1-(4-toluenesulfonyl)indol-3-yl}propenoate

: 38614-36-7
2-methylpropen-1-ylmagnesium bromide

: 862297-62-9
ethyl 5-methyl-3-{[4-(tert-butyldiphenylsilyloxy)methyl]-1-(4-toluenesulfonyl)indol-3-yl}hex-4-enoate

Guidance literature:: 2-methylpropen-1-ylmagnesium bromide; With copper(I) thiophenolate; In tetrahydrofuran; at -40 - 0 ℃; for 1h;

ethyl (E)-3-{4-[(tert-butyldiphenylsilyloxy)methyl]-1-(4-toluenesulfonyl)indol-3-yl}propenoate; In tetrahydrofuran; at -40 - 20 ℃; Further stages.;
DOI:10.1039/b417625c

Reference yield:

: 1074-85-7
(1H-indol-4-yl)methanol

: 862297-62-9
ethyl 5-methyl-3-{[4-(tert-butyldiphenylsilyloxy)methyl]-1-(4-toluenesulfonyl)indol-3-yl}hex-4-enoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 95 percent / imidazole / tetrahydrofuran / 16 h / 20 °C

2.1: 82 percent / POCl₃ / pyridine / 0.75 h / 35 °C

3.1: 85 percent / Et₃N; DMAP / CH₂Cl₂ / 16 h / 20 °C

4.1: LiCl; DBN / acetonitrile / 0.25 h / 20 °C

4.2: 62 percent / acetonitrile / 2 h / 20 °C

5.1: PhSCu / tetrahydrofuran / 1 h / -40 - 0 °C

5.2: 53 percent / tetrahydrofuran / -40 - 20 °C

With 1H-imidazole; dmap; 2,6-dichloro-benzonitrile; copper(I) thiophenolate; triethylamine; lithium chloride; trichlorophosphate; In tetrahydrofuran; pyridine; dichloromethane; acetonitrile; 4.2: Horner-Wadsworth-Emmons reaction / 5.2: Michael addition;
DOI:10.1039/b417625c

Reference yield:

: 862297-60-7
4-[(tert-butyldiphenylsilyloxy)methyl]indole

: 862297-62-9
ethyl 5-methyl-3-{[4-(tert-butyldiphenylsilyloxy)methyl]-1-(4-toluenesulfonyl)indol-3-yl}hex-4-enoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 82 percent / POCl₃ / pyridine / 0.75 h / 35 °C

2.1: 85 percent / Et₃N; DMAP / CH₂Cl₂ / 16 h / 20 °C

3.1: LiCl; DBN / acetonitrile / 0.25 h / 20 °C

3.2: 62 percent / acetonitrile / 2 h / 20 °C

4.1: PhSCu / tetrahydrofuran / 1 h / -40 - 0 °C

4.2: 53 percent / tetrahydrofuran / -40 - 20 °C

With dmap; 2,6-dichloro-benzonitrile; copper(I) thiophenolate; triethylamine; lithium chloride; trichlorophosphate; In tetrahydrofuran; pyridine; dichloromethane; acetonitrile; 3.2: Horner-Wadsworth-Emmons reaction / 4.2: Michael addition;
DOI:10.1039/b417625c