6-{2-[(1S,3S)-3-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-methylidenecyclohexyl]ethyl}-1,4-dimethoxynaphthalene

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Chemical Name:6-{2-[(1S,3S)-3-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-methylidenecyclohexyl]ethyl}-1,4-dimethoxynaphthalene
CAS No.:615562-19-1
Molecular Formula:C₂₉H₄₄O₃Si
Molecular Weight:468.752
Hs Code.:

Synonyms:6-{2-[(1S,3S)-3-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-methylidenecyclohexyl]ethyl}-1,4-dimethoxynaphthalene

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Chemical Property of 6-{2-[(1S,3S)-3-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-methylidenecyclohexyl]ethyl}-1,4-dimethoxynaphthalene

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Technology Process of 6-{2-[(1S,3S)-3-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-methylidenecyclohexyl]ethyl}-1,4-dimethoxynaphthalene

There total 5 articles about 6-{2-[(1S,3S)-3-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-methylidenecyclohexyl]ethyl}-1,4-dimethoxynaphthalene 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: 43.0%

: 91270-71-2
6-bromo-1,4-dimethoxynaphthalene

: 615562-18-0
2-[(1S,3S)-3-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-methylidenecyclohexyl]iodoethane

: 615562-19-1
6-{2-[(1S,3S)-3-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-methylidenecyclohexyl]ethyl}-1,4-dimethoxynaphthalene

Guidance literature:: 2-[(1S,3S)-3-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-methylidenecyclohexyl]iodoethane; With tert.-butyl lithium; In diethyl ether; at -78 ℃;

With 9-methoxy-9-BBN; In tetrahydrofuran; diethyl ether; hexane;

6-bromo-1,4-dimethoxynaphthalene; With potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; diethyl ether; hexane; at 80 ℃; for 16h;
DOI:10.1016/S0040-4039(03)01669-1

Reference yield:

: 71127-64-5
6-bromonaphthalene-1,4-dione

: 615562-19-1
6-{2-[(1S,3S)-3-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-methylidenecyclohexyl]ethyl}-1,4-dimethoxynaphthalene

Guidance literature:: Multi-step reaction with 3 steps

1.1: H₂ / PtO₂ / ethyl acetate

2.1: NaH / dimethylformamide

3.1: tert-BuLi / diethyl ether / -78 °C

3.2: B-methoxy-9-borabicyclo[3.3.1]-nonane / diethyl ether; hexane; tetrahydrofuran

3.3: 43 percent / K₃PO₄ / Pd(PPh₃)4 / diethyl ether; hexane; tetrahydrofuran / 16 h / 80 °C

With hydrogen; tert.-butyl lithium; sodium hydride; platinum(IV) oxide; In diethyl ether; ethyl acetate; N,N-dimethyl-formamide; 3.1: B-alkyl Suzuki-Miyaura coupling / 3.2: B-alkyl Suzuki-Miyaura coupling / 3.3: B-alkyl Suzuki-Miyaura coupling;
DOI:10.1016/S0040-4039(03)01669-1

Reference yield:

: 124263-03-2
(1S,3S)-3-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-methylenecyclohexaneethanol

: 615562-19-1
6-{2-[(1S,3S)-3-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-methylidenecyclohexyl]ethyl}-1,4-dimethoxynaphthalene

Guidance literature:: Multi-step reaction with 3 steps

1.1: pyridine / 4 °C

2.1: 5.91 g / NaI / acetone / 4 h / Heating

3.1: t-BuLi; 9-methoxy-9-borabicyclo[3.3.1]nonane / various solvents / 1.42 h / -78 - 20 °C

3.2: 40 percent / K₃PO₄ / [Pd(PPh₃)4] / various solvents / 16 h / 80 °C

With pyridine; tert.-butyl lithium; 9-methoxy-9-BBN; sodium iodide; In various solvents; acetone; 3.2: Suzuki-Miyaura coupling;
DOI:10.1016/j.tet.2005.06.115