[2-bromo-3-(tert-butyl-dimethyl-silanyloxy)-6,6-dimethyl-cyclohex-1-enyl]-methanol

Base Information

Chemical Name:[2-bromo-3-(tert-butyl-dimethyl-silanyloxy)-6,6-dimethyl-cyclohex-1-enyl]-methanol
CAS No.:444809-27-2
Molecular Formula:C₁₅H₂₉BrO₂Si
Molecular Weight:349.384
Hs Code.:

[2-bromo-3-(<i>tert</i>-butyl-dimethyl-silanyloxy)-6,6-dimethyl-cyclohex-1-enyl]-methanol

Synonyms:[2-bromo-3-(tert-butyl-dimethyl-silanyloxy)-6,6-dimethyl-cyclohex-1-enyl]-methanol

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Chemical Property of [2-bromo-3-(tert-butyl-dimethyl-silanyloxy)-6,6-dimethyl-cyclohex-1-enyl]-methanol

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Technology Process of [2-bromo-3-(tert-butyl-dimethyl-silanyloxy)-6,6-dimethyl-cyclohex-1-enyl]-methanol

There total 6 articles about [2-bromo-3-(tert-butyl-dimethyl-silanyloxy)-6,6-dimethyl-cyclohex-1-enyl]-methanol 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: 70.0%

: 444809-19-2
(1R)-2-bromo-3-methoxymethoxymethyl-4,4-dimethyl-cyclohex-2-enyloxy-tert-butyl-dimethyl-silane

: 444809-27-2
[2-bromo-3-(tert-butyl-dimethyl-silanyloxy)-6,6-dimethyl-cyclohex-1-enyl]-methanol

Guidance literature:: With n-butanethiol; magnesium bromide; In diethyl ether; at 20 ℃; for 12h;
DOI:10.1021/ol026159t

Reference yield:

: 6553-64-6
6,6-Dimethyl-2-cyclohexen-1-one

: 444809-27-2
[2-bromo-3-(tert-butyl-dimethyl-silanyloxy)-6,6-dimethyl-cyclohex-1-enyl]-methanol

Guidance literature:: Multi-step reaction with 6 steps

1: 78 percent / n-BuLi / tetrahydrofuran / 0.5 h / -78 °C

2: 90 percent / PCC / CH₂Cl₂ / 12 h / 20 °C

3: 60 percent / pyridinium tribromide; pyridine / CH₂Cl₂ / 20 h / 20 - 40 °C

4: 92 percent / (S)-CBS; BH₃*THF / tetrahydrofuran / 2 h / 20 °C

5: 85 percent / imidazole / dimethylformamide / 2 h / 20 - 40 °C

6: 70 percent / MgBr₂*Et₂O; BuSH / diethyl ether / 12 h / 20 °C

With pyridine; 1H-imidazole; n-butyllithium; borane-THF; (S)-diphenylprolinol; n-butanethiol; pyridinium hydrobromide perbromide; pyridinium chlorochromate; magnesium bromide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol026159t

Reference yield:

: 444809-15-8
1-methoxymethoxymethyl-6,6-dimethyl-cyclohex-2-enol

: 444809-27-2
[2-bromo-3-(tert-butyl-dimethyl-silanyloxy)-6,6-dimethyl-cyclohex-1-enyl]-methanol

Guidance literature:: Multi-step reaction with 5 steps

1: 90 percent / PCC / CH₂Cl₂ / 12 h / 20 °C

2: 60 percent / pyridinium tribromide; pyridine / CH₂Cl₂ / 20 h / 20 - 40 °C

3: 92 percent / (S)-CBS; BH₃*THF / tetrahydrofuran / 2 h / 20 °C

4: 85 percent / imidazole / dimethylformamide / 2 h / 20 - 40 °C

5: 70 percent / MgBr₂*Et₂O; BuSH / diethyl ether / 12 h / 20 °C

With pyridine; 1H-imidazole; borane-THF; (S)-diphenylprolinol; n-butanethiol; pyridinium hydrobromide perbromide; pyridinium chlorochromate; magnesium bromide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol026159t