3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-cyclohex-3-enone

Base Information

• Chemical Name: 3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-cyclohex-3-enone
• CAS No.: 256469-27-9
• Molecular Formula: C₁₆H₃₀O₂Si
• Molecular Weight: 282.498
• Mol file: 256469-27-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about 3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-cyclohex-3-enone 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: 99.0%

tert-butyldimethylsilyl chloride (18162-48-6) + 3-(2-hydroxyethyl)-2,2-dimethylcyclohex-3-en-1-one (256469-26-8) → 3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-cyclohex-3-enone (256469-27-9)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 15h;

DOI:10.1002/(SICI)1099-0690(199912)1999:12<3241::AID-EJOC3241>3.0.CO;2-9

Reference yield:

ethylene glycole monoacetal of 2,2-dimethylcyclohexane-1,3-dione (14782-52-6) → 3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-cyclohex-3-enone (256469-27-9)

Guidance literature:

Multi-step reaction with 5 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

With dmap; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; dihydrogen peroxide; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium chloride; lithium hexamethyldisilazane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; ethanol; dichloromethane; water; 1: Substitution / 2: Substitution / 3: hydroboration / 4: Elimination / 5: silylation;

DOI:10.1002/(SICI)1099-0690(199912)1999:12<3241::AID-EJOC3241>3.0.CO;2-9

Reference yield:

6,6-dimethyl-1,4-dioxaspiro[4.5]dec-7-en-7-yl trifluoromethanesulfonate (256469-23-5) → 3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-cyclohex-3-enone (256469-27-9)

Guidance literature:

Multi-step reaction with 4 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

With dmap; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; dihydrogen peroxide; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; ethanol; dichloromethane; water; 1: Substitution / 2: hydroboration / 3: Elimination / 4: silylation;

DOI:10.1002/(SICI)1099-0690(199912)1999:12<3241::AID-EJOC3241>3.0.CO;2-9

upstream raw materials:

tert-butyldimethylsilyl chloride

3-(2-hydroxyethyl)-2,2-dimethylcyclohex-3-en-1-one

ethylene glycole monoacetal of 2,2-dimethylcyclohexane-1,3-dione

6,6-dimethyl-7-ethenyl-1,4-dioxaspiro[4.5]dec-7-ene

Downstream raw materials:

1-cyclohex-2-enylmethyl-3-(2-hydroxy-ethyl)-2,2-dimethyl-cyclohex-3-enol

1-cyclohex-2-enylmethyl-3-(2-iodo-ethyl)-2,2-dimethyl-cyclohex-3-enol

1-but-3-enyl-3-(2-iodo-ethyl)-2,2-dimethyl-cyclohex-3-enol

(5-cyclohex-2-enylmethyl-5-hydroxy-6,6-dimethyl-cyclohex-1-enyl)-acetaldehyde