(1S,3S)-3-[2-(5,8-Dimethoxy-naphthalen-2-yl)-ethyl]-2,2-dimethyl-4-methylene-cyclohexanol

Base Information

Chemical Name:(1S,3S)-3-[2-(5,8-Dimethoxy-naphthalen-2-yl)-ethyl]-2,2-dimethyl-4-methylene-cyclohexanol
CAS No.:615562-21-5
Molecular Formula:C₂₃H₃₀O₃
Molecular Weight:354.489
Hs Code.:

Synonyms:(1S,3S)-3-[2-(5,8-Dimethoxy-naphthalen-2-yl)-ethyl]-2,2-dimethyl-4-methylene-cyclohexanol

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Chemical Property of (1S,3S)-3-[2-(5,8-Dimethoxy-naphthalen-2-yl)-ethyl]-2,2-dimethyl-4-methylene-cyclohexanol

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Technology Process of (1S,3S)-3-[2-(5,8-Dimethoxy-naphthalen-2-yl)-ethyl]-2,2-dimethyl-4-methylene-cyclohexanol

There total 7 articles about (1S,3S)-3-[2-(5,8-Dimethoxy-naphthalen-2-yl)-ethyl]-2,2-dimethyl-4-methylene-cyclohexanol 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: 93.0%

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

: 615562-21-5
(1S,3S)-3-[2-(5,8-Dimethoxy-naphthalen-2-yl)-ethyl]-2,2-dimethyl-4-methylene-cyclohexanol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 50 - 60 ℃; for 6h;
DOI:10.1016/j.tet.2005.06.115

Reference yield:

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

: 615562-21-5
(1S,3S)-3-[2-(5,8-Dimethoxy-naphthalen-2-yl)-ethyl]-2,2-dimethyl-4-methylene-cyclohexanol

Guidance literature:: Multi-step reaction with 4 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

4.1: 74 percent / TBAF / tetrahydrofuran / 60 °C

With tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; sodium hydride; platinum(IV) oxide; In tetrahydrofuran; 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

: 615562-21-5
(1S,3S)-3-[2-(5,8-Dimethoxy-naphthalen-2-yl)-ethyl]-2,2-dimethyl-4-methylene-cyclohexanol

Guidance literature:: Multi-step reaction with 4 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

4.1: 93 percent / TBAF / tetrahydrofuran / 6 h / 50 - 60 °C

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