(S,E)-tert-butyldimethylsilyl 4-(but-1-en-3-yn-1-yl)-3,5,5-trimethylcyclohex-3-en-1-yl ether

Base Information

Chemical Name:(S,E)-tert-butyldimethylsilyl 4-(but-1-en-3-yn-1-yl)-3,5,5-trimethylcyclohex-3-en-1-yl ether
CAS No.:444122-14-9
Molecular Formula:C₁₉H₃₂OSi
Molecular Weight:304.548
Hs Code.:

Synonyms:(S,E)-tert-butyldimethylsilyl 4-(but-1-en-3-yn-1-yl)-3,5,5-trimethylcyclohex-3-en-1-yl ether

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Chemical Property of (S,E)-tert-butyldimethylsilyl 4-(but-1-en-3-yn-1-yl)-3,5,5-trimethylcyclohex-3-en-1-yl ether

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Technology Process of (S,E)-tert-butyldimethylsilyl 4-(but-1-en-3-yn-1-yl)-3,5,5-trimethylcyclohex-3-en-1-yl ether

There total 8 articles about (S,E)-tert-butyldimethylsilyl 4-(but-1-en-3-yn-1-yl)-3,5,5-trimethylcyclohex-3-en-1-yl ether 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: 67.0%

: 83021-07-2
(S,E)-4-[4-(tert-butyldimethylsilyloxy)-2,6,6-trimethylcyclohex-1-en-1-yl]but-3-en-2-one

: 444122-14-9
(S,E)-tert-butyldimethylsilyl 4-(but-1-en-3-yn-1-yl)-3,5,5-trimethylcyclohex-3-en-1-yl ether

Guidance literature:: (S,E)-4-[4-(tert-butyldimethylsilyloxy)-2,6,6-trimethylcyclohex-1-en-1-yl]but-3-en-2-one; With n-butyllithium; diisopropylamine; In tetrahydrofuran; at -78 ℃; for 1.5h;

With diethyl chlorophosphate; In tetrahydrofuran; at 20 ℃; for 3h;

With lithium diisopropyl amide; In tetrahydrofuran; at 20 ℃; for 13h; Further stages.;
DOI:10.1021/jo025727f

Reference yield:

: 444122-13-8
tert-butyldimethylsilyl (R)-4-iodo-3,5,5-trimethylcyclohex-3-en-1-yl ether

: 444122-14-9
(S,E)-tert-butyldimethylsilyl 4-(but-1-en-3-yn-1-yl)-3,5,5-trimethylcyclohex-3-en-1-yl ether

Guidance literature:: Multi-step reaction with 2 steps

1.1: 90 percent / Pd(PPh₃)4; Et₃N / dimethylformamide / 13 h / 75 °C

2.1: nBuLi; iPr₂NH / tetrahydrofuran / 1.5 h / -78 °C

2.2: ClPO(OEt)2 / tetrahydrofuran / 3 h / 20 °C

2.3: 67 percent / LDA / tetrahydrofuran / 13 h / 20 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; triethylamine; diisopropylamine; In tetrahydrofuran; N,N-dimethyl-formamide; 1.1: Heck coupling;
DOI:10.1021/jo025727f

Reference yield:

: 20548-02-1,55058-51-0,60686-81-9,60686-82-0,82977-53-5,90082-06-7,90129-05-8,99881-84-2,60046-50-6
(4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexan-1-one

: 444122-14-9
(S,E)-tert-butyldimethylsilyl 4-(but-1-en-3-yn-1-yl)-3,5,5-trimethylcyclohex-3-en-1-yl ether

Guidance literature:: Multi-step reaction with 5 steps

1.1: 83 percent / imidazole / dimethylformamide / 6 h / 0 °C

2.1: NH₂NH₂*H₂O; Et₃N / ethanol / 24 h / 100 °C

3.1: DBN; I₂ / diethyl ether / 0.25 h

3.2: 0.563 g / DBN / benzene / 2.5 h

4.1: 90 percent / Pd(PPh₃)4; Et₃N / dimethylformamide / 13 h / 75 °C

5.1: nBuLi; iPr₂NH / tetrahydrofuran / 1.5 h / -78 °C

5.2: ClPO(OEt)2 / tetrahydrofuran / 3 h / 20 °C

5.3: 67 percent / LDA / tetrahydrofuran / 13 h / 20 °C

With 1H-imidazole; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; 2,6-dichloro-benzonitrile; iodine; hydrazine hydrate; triethylamine; diisopropylamine; In tetrahydrofuran; diethyl ether; ethanol; N,N-dimethyl-formamide; 4.1: Heck coupling;
DOI:10.1021/jo025727f