2-Bromo-3-dimethoxymethyl-5-triisopropylsilanyloxymethyl-cyclohex-2-enone

Base Information

• Chemical Name: 2-Bromo-3-dimethoxymethyl-5-triisopropylsilanyloxymethyl-cyclohex-2-enone
• CAS No.: 157428-06-3
• Molecular Formula: C₁₉H₃₅BrO₄Si
• Molecular Weight: 435.474
• Mol file: 157428-06-3.mol

Synonyms:2-Bromo-3-dimethoxymethyl-5-triisopropylsilanyloxymethyl-cyclohex-2-enone

Chemical Property of 2-Bromo-3-dimethoxymethyl-5-triisopropylsilanyloxymethyl-cyclohex-2-enone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Bromo-3-dimethoxymethyl-5-triisopropylsilanyloxymethyl-cyclohex-2-enone

There total 6 articles about 2-Bromo-3-dimethoxymethyl-5-triisopropylsilanyloxymethyl-cyclohex-2-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: 86.0%

methanol (67-56-1) + 2-Bromo-3-(methoxy-phenylsulfanyl-methyl)-5-triisopropylsilanyloxymethyl-cyclohex-2-enone (157428-04-1) → 2-Bromo-3-dimethoxymethyl-5-triisopropylsilanyloxymethyl-cyclohex-2-enone (157428-06-3)

Guidance literature:

copper(II) oxide; copper dichloride; for 2h; Heating;

DOI:10.1016/S0040-4020(01)85633-7

Reference yield:

(3,5-dimethoxycyclohexa-2,5-dien-1-yl)methanol (90612-16-1) → 2-Bromo-3-dimethoxymethyl-5-triisopropylsilanyloxymethyl-cyclohex-2-enone (157428-06-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 70 percent / conc. H₂SO₄ / 0.33 h / 0 °C

2: 94 percent / NBS / CH₂Cl₂ / 0 °C

3: BF₃*OEt₂ / 0.83 h / 0 °C

4: 1.) NaOMe; 2.) imidazole / 1.) methanol, 0 degC, 40 min; 2.) DMF, room t., 2 h

5: 1.) n-BuLi; 2.) HClO₄ / 1.) THF, hexane, -78 degC, 1 h; 2.) ether, AcOEt, water, room t., 5 min

6: 86 percent / CuCl₂, CuO / 2 h / Heating

With 1H-imidazole; N-Bromosuccinimide; n-butyllithium; perchloric acid; sulfuric acid; boron trifluoride diethyl etherate; sodium methylate; copper(II) oxide; copper dichloride; In dichloromethane;

DOI:10.1016/S0040-4020(01)85633-7

Reference yield:

5-Hydroxymethyl-3-isobutoxy-cyclohex-2-enone (207921-97-9) → 2-Bromo-3-dimethoxymethyl-5-triisopropylsilanyloxymethyl-cyclohex-2-enone (157428-06-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 94 percent / NBS / CH₂Cl₂ / 0 °C

2: BF₃*OEt₂ / 0.83 h / 0 °C

3: 1.) NaOMe; 2.) imidazole / 1.) methanol, 0 degC, 40 min; 2.) DMF, room t., 2 h

4: 1.) n-BuLi; 2.) HClO₄ / 1.) THF, hexane, -78 degC, 1 h; 2.) ether, AcOEt, water, room t., 5 min

5: 86 percent / CuCl₂, CuO / 2 h / Heating

With 1H-imidazole; N-Bromosuccinimide; n-butyllithium; perchloric acid; boron trifluoride diethyl etherate; sodium methylate; copper(II) oxide; copper dichloride; In dichloromethane;

DOI:10.1016/S0040-4020(01)85633-7

upstream raw materials:

methanol

2-Bromo-3-(methoxy-phenylsulfanyl-methyl)-5-triisopropylsilanyloxymethyl-cyclohex-2-enone

(3,5-dimethoxycyclohexa-2,5-dien-1-yl)methanol

5-Hydroxymethyl-3-isobutoxy-cyclohex-2-enone

Downstream raw materials:

[4-(tert-Butyl-dimethyl-silanyloxy)-2-(2-dimethoxymethyl-6-oxo-4-triisopropylsilanyloxymethyl-cyclohex-1-enyl)-phenyl]-carbamic acid tert-butyl ester

[2-(2-Dimethoxymethyl-6-oxo-4-triisopropylsilanyloxymethyl-cyclohex-1-enyl)-phenyl]-carbamic acid tert-butyl ester