4-(tert-butyldimethylsilyloxy)-1-cyano-2,6,6-trimethylcyclohex-3-enecarboxylic acid ethyl ester

Base Information

Chemical Name:4-(tert-butyldimethylsilyloxy)-1-cyano-2,6,6-trimethylcyclohex-3-enecarboxylic acid ethyl ester
CAS No.:1307740-37-9
Molecular Formula:C₁₉H₃₃NO₃Si
Molecular Weight:351.561
Hs Code.:

Synonyms:4-(tert-butyldimethylsilyloxy)-1-cyano-2,6,6-trimethylcyclohex-3-enecarboxylic acid ethyl ester

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Chemical Property of 4-(tert-butyldimethylsilyloxy)-1-cyano-2,6,6-trimethylcyclohex-3-enecarboxylic acid ethyl ester

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Technology Process of 4-(tert-butyldimethylsilyloxy)-1-cyano-2,6,6-trimethylcyclohex-3-enecarboxylic acid ethyl ester

There total 1 articles about 4-(tert-butyldimethylsilyloxy)-1-cyano-2,6,6-trimethylcyclohex-3-enecarboxylic acid 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:

: 153010-77-6
2-tert-buthyldimethylsilyloxy-1,3-pentadiene

: 759-58-0
ethyl isopropylidenecyanoacetate

: 1-[(1R*,2S*,6S*)-4-(tert-butyldimethylsilyloxy)-2,6-dimethylcyclohex-3-enyl]ethanone

: 1307740-37-9
4-(tert-butyldimethylsilyloxy)-1-cyano-2,6,6-trimethylcyclohex-3-enecarboxylic acid ethyl ester

Guidance literature:: ethyl isopropylidenecyanoacetate; With zinc(II) chloride; In toluene; for 0.5h; Inert atmosphere;

2-tert-buthyldimethylsilyloxy-1,3-pentadiene; In toluene; at 80 ℃; for 20h; Inert atmosphere;
DOI:10.1055/s-0030-1258412

Reference yield: 70.0%

: 5162-44-7
1-bromo-4-butene

: 1307740-37-9
4-(tert-butyldimethylsilyloxy)-1-cyano-2,6,6-trimethylcyclohex-3-enecarboxylic acid ethyl ester

: (1S*,2S*)-1-but-3-enyl-4-(tert-butyldimethylsilyloxy)-2,6,6-trimethylcyclohex-3-enecarboxylic acid

Guidance literature:: 4-(tert-butyldimethylsilyloxy)-1-cyano-2,6,6-trimethylcyclohex-3-enecarboxylic acid ethyl ester; With lithium dihydronaphthylide radical; In tetrahydrofuran; at -45 ℃; for 0.5h; Inert atmosphere;

1-bromo-4-butene; With N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; at 20 ℃; for 12h; Inert atmosphere;
DOI:10.1055/s-0030-1258412

Reference yield:

: 1307740-37-9
4-(tert-butyldimethylsilyloxy)-1-cyano-2,6,6-trimethylcyclohex-3-enecarboxylic acid ethyl ester

: C₂₀H₃₆O₃Si

Guidance literature:: Multi-step reaction with 7 steps

1.1: lithium dihydronaphthylide radical / tetrahydrofuran / 0.5 h / -45 °C / Inert atmosphere

1.2: 12 h / 20 °C / Inert atmosphere

2.1: 2,6-dimethylpyridine; 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 24 h / 20 °C / Inert atmosphere

3.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol; dichloromethane / 1 h / 0 °C

4.1: 1H-imidazole / N,N-dimethyl-formamide / 12 h / Inert atmosphere

5.1: oxygen; copper(l) chloride; palladium dichloride / tetrahydrofuran; water; N,N-dimethyl-formamide / 18 h

6.1: lithium aluminium tetrahydride / tetrahydrofuran / 5 h / 0 - 20 °C / Inert atmosphere

7.1: pyridinium chlorochromate / dichloromethane / 12 h / 20 °C / Inert atmosphere

With 1H-imidazole; 2,6-dimethylpyridine; sodium tetrahydroborate; lithium aluminium tetrahydride; cerium(III) chloride heptahydrate; oxygen; lithium dihydronaphthylide radical; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; copper(l) chloride; palladium dichloride; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; benzene; 5.1: Wacker oxidation;
DOI:10.1055/s-0030-1258412