1-allyl-3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-cyclohex-3-enol

Base Information

Chemical Name:1-allyl-3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-cyclohex-3-enol
CAS No.:256469-31-5
Molecular Formula:C₁₉H₃₆O₂Si
Molecular Weight:324.579
Hs Code.:

1-allyl-3-[2-(<i>tert</i>-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-cyclohex-3-enol

Synonyms:1-allyl-3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-cyclohex-3-enol

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Chemical Property of 1-allyl-3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-cyclohex-3-enol

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Technology Process of 1-allyl-3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-cyclohex-3-enol

There total 7 articles about 1-allyl-3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-cyclohex-3-enol 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: 97.0%

: 106-95-6
allyl bromide

: 256469-27-9
3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-cyclohex-3-enone

: 256469-31-5
1-allyl-3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-cyclohex-3-enol

Guidance literature:: With copper; zinc; In tetrahydrofuran; under 35 Torr; Heating;
DOI:10.1002/(SICI)1099-0690(199912)1999:12<3241::AID-EJOC3241>3.0.CO;2-9

Reference yield:

: 14782-52-6
ethylene glycole monoacetal of 2,2-dimethylcyclohexane-1,3-dione

: 256469-31-5
1-allyl-3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-cyclohex-3-enol

Guidance literature:: Multi-step reaction with 6 steps

1: 85 percent / LiHMDS / tetrahydrofuran / 3 h / 0 °C

2: 95 percent / LiCl; DBU / Pd(PPh₃)4 / tetrahydrofuran / 20 °C / Heating

3: 100 percent / 9-BBN; H₂O₂; NaOH / tetrahydrofuran; ethanol / 3 h / Heating

4: 99 percent / TsOH / tetrahydrofuran; H₂O / 18 h / Heating

5: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 15 h / 20 °C

6: 97 percent / Zn-Cu complex / tetrahydrofuran / 35 Torr / Heating

With dmap; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; dihydrogen peroxide; copper; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium chloride; lithium hexamethyldisilazane; zinc; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; ethanol; dichloromethane; water; 1: Substitution / 2: Substitution / 3: hydroboration / 4: Elimination / 5: silylation / 6: Barbier-type coupling;
DOI:10.1002/(SICI)1099-0690(199912)1999:12<3241::AID-EJOC3241>3.0.CO;2-9

Reference yield:

: 256469-23-5
6,6-dimethyl-1,4-dioxaspiro[4.5]dec-7-en-7-yl trifluoromethanesulfonate

: 256469-31-5
1-allyl-3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-cyclohex-3-enol

Guidance literature:: Multi-step reaction with 5 steps

1: 95 percent / LiCl; DBU / Pd(PPh₃)4 / tetrahydrofuran / 20 °C / Heating

2: 100 percent / 9-BBN; H₂O₂; NaOH / tetrahydrofuran; ethanol / 3 h / Heating

3: 99 percent / TsOH / tetrahydrofuran; H₂O / 18 h / Heating

4: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 15 h / 20 °C

5: 97 percent / Zn-Cu complex / tetrahydrofuran / 35 Torr / Heating

With dmap; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; dihydrogen peroxide; copper; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium chloride; zinc; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; ethanol; dichloromethane; water; 1: Substitution / 2: hydroboration / 3: Elimination / 4: silylation / 5: Barbier-type coupling;
DOI:10.1002/(SICI)1099-0690(199912)1999:12<3241::AID-EJOC3241>3.0.CO;2-9