(R)-4-((1E,3E)-4-iodo-3-methylbuta-1,3-dien-1-yl)-3,5,5-trimethylcyclohex-3-en-1-ol

Base Information

Chemical Name:(R)-4-((1E,3E)-4-iodo-3-methylbuta-1,3-dien-1-yl)-3,5,5-trimethylcyclohex-3-en-1-ol
CAS No.:444122-16-1
Molecular Formula:C₁₄H₂₁IO
Molecular Weight:332.225
Hs Code.:

Synonyms:(R)-4-((1E,3E)-4-iodo-3-methylbuta-1,3-dien-1-yl)-3,5,5-trimethylcyclohex-3-en-1-ol

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Chemical Property of (R)-4-((1E,3E)-4-iodo-3-methylbuta-1,3-dien-1-yl)-3,5,5-trimethylcyclohex-3-en-1-ol

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Technology Process of (R)-4-((1E,3E)-4-iodo-3-methylbuta-1,3-dien-1-yl)-3,5,5-trimethylcyclohex-3-en-1-ol

There total 8 articles about (R)-4-((1E,3E)-4-iodo-3-methylbuta-1,3-dien-1-yl)-3,5,5-trimethylcyclohex-3-en-1-ol 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: 69.0%

: 75-24-1
trimethylaluminum

: 444122-15-0
(S)-4-[(E)-but-1-en-3-ynyl]-3,5,5-trimethylcyclohex-3-en-1-ol

: 444122-16-1
(R)-4-((1E,3E)-4-iodo-3-methylbuta-1,3-dien-1-yl)-3,5,5-trimethylcyclohex-3-en-1-ol

Guidance literature:: trimethylaluminum; (S)-4-[(E)-but-1-en-3-ynyl]-3,5,5-trimethylcyclohex-3-en-1-ol; zirconocene dichloride; In dichloromethane; at 20 ℃; for 12h;

With iodine; In tetrahydrofuran; dichloromethane; at -40 ℃; Further stages.;
DOI:10.1021/jo025727f

Reference yield:

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

: 444122-16-1
(R)-4-((1E,3E)-4-iodo-3-methylbuta-1,3-dien-1-yl)-3,5,5-trimethylcyclohex-3-en-1-ol

Guidance literature:: Multi-step reaction with 3 steps

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

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

1.3: 67 percent / LDA / tetrahydrofuran / 13 h / 20 °C

2.1: 96 percent / (nBu)4NF / tetrahydrofuran / 2.5 h / 20 °C

3.1: Cp₂ZrCl₂ / CH₂Cl₂ / 12 h / 20 °C

3.2: 69 percent / I₂ / CH₂Cl₂; tetrahydrofuran / -40 °C

With n-butyllithium; tetrabutyl ammonium fluoride; diisopropylamine; zirconocene dichloride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo025727f

Reference yield:

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

: 444122-16-1
(R)-4-((1E,3E)-4-iodo-3-methylbuta-1,3-dien-1-yl)-3,5,5-trimethylcyclohex-3-en-1-ol

Guidance literature:: Multi-step reaction with 4 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

3.1: 96 percent / (nBu)4NF / tetrahydrofuran / 2.5 h / 20 °C

4.1: Cp₂ZrCl₂ / CH₂Cl₂ / 12 h / 20 °C

4.2: 69 percent / I₂ / CH₂Cl₂; tetrahydrofuran / -40 °C

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