5-(tert-Butyldimethylsilyloxy)-N,N-dimethyl-2-(tetrahydropyran-2-yloxy)benzamide

Base Information

Chemical Name:5-(tert-Butyldimethylsilyloxy)-N,N-dimethyl-2-(tetrahydropyran-2-yloxy)benzamide
CAS No.:299917-43-4
Molecular Formula:C₂₀H₃₃NO₄Si
Molecular Weight:379.572
Hs Code.:

Synonyms:5-(tert-Butyldimethylsilyloxy)-N,N-dimethyl-2-(tetrahydropyran-2-yloxy)benzamide

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Chemical Property of 5-(tert-Butyldimethylsilyloxy)-N,N-dimethyl-2-(tetrahydropyran-2-yloxy)benzamide

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Technology Process of 5-(tert-Butyldimethylsilyloxy)-N,N-dimethyl-2-(tetrahydropyran-2-yloxy)benzamide

There total 5 articles about 5-(tert-Butyldimethylsilyloxy)-N,N-dimethyl-2-(tetrahydropyran-2-yloxy)benzamide 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: 85.0%

: 299917-31-0
[4-(Tetrahydropyran-2-yloxy)phenoxy]-tert-butyldimethylsilane

: 79-44-7
N,N-Dimethylcarbamoyl chloride

: 299917-43-4
5-(tert-Butyldimethylsilyloxy)-N,N-dimethyl-2-(tetrahydropyran-2-yloxy)benzamide

Guidance literature:: [4-(Tetrahydropyran-2-yloxy)phenoxy]-tert-butyldimethylsilane; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 0.75h;

N,N-Dimethylcarbamoyl chloride; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 4h; Further stages.;
DOI:10.1002/1521-3765(20000804)6:15<2874::AID-CHEM2874>3.0.CO;2-1

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 299917-43-4
5-(tert-Butyldimethylsilyloxy)-N,N-dimethyl-2-(tetrahydropyran-2-yloxy)benzamide

Guidance literature:: Multi-step reaction with 3 steps

1.1: 64 percent / imidazole / dimethylformamide / 17 h / 20 °C

2.1: 93 percent / PPTS / CH₂Cl₂ / 4.5 h / 20 °C

3.1: nBuLi / tetrahydrofuran; hexane / 0.75 h / -78 - 20 °C

3.2: 85 percent / tetrahydrofuran; hexane / 4 h / -78 - 20 °C

With 1H-imidazole; n-butyllithium; pyridinium p-toluenesulfonate; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; 1.1: Etherification / 2.1: Addition / 3.1: Metallation / 3.2: Substitution;
DOI:10.1002/1521-3765(20000804)6:15<2874::AID-CHEM2874>3.0.CO;2-1

Reference yield:

: 108534-47-0
4-(tert-butyldimethylsilyloxy)phenol

: 299917-43-4
5-(tert-Butyldimethylsilyloxy)-N,N-dimethyl-2-(tetrahydropyran-2-yloxy)benzamide

Guidance literature:: Multi-step reaction with 2 steps

1.1: 93 percent / PPTS / CH₂Cl₂ / 4.5 h / 20 °C

2.1: nBuLi / tetrahydrofuran; hexane / 0.75 h / -78 - 20 °C

2.2: 85 percent / tetrahydrofuran; hexane / 4 h / -78 - 20 °C

With n-butyllithium; pyridinium p-toluenesulfonate; In tetrahydrofuran; hexane; dichloromethane; 1.1: Addition / 2.1: Metallation / 2.2: Substitution;
DOI:10.1002/1521-3765(20000804)6:15<2874::AID-CHEM2874>3.0.CO;2-1