5-(2-Bromo-1-methoxy-ethoxymethyl)-3-methoxy-5-vinyl-cyclohex-2-enone

Base Information

• Chemical Name: 5-(2-Bromo-1-methoxy-ethoxymethyl)-3-methoxy-5-vinyl-cyclohex-2-enone
• CAS No.: 66556-44-3
• Molecular Formula: C₁₃H₁₉BrO₄
• Molecular Weight: 319.195
• Mol file: 66556-44-3.mol

Synonyms:5-(2-Bromo-1-methoxy-ethoxymethyl)-3-methoxy-5-vinyl-cyclohex-2-enone

Chemical Property of 5-(2-Bromo-1-methoxy-ethoxymethyl)-3-methoxy-5-vinyl-cyclohex-2-enone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-(2-Bromo-1-methoxy-ethoxymethyl)-3-methoxy-5-vinyl-cyclohex-2-enone

There total 13 articles about 5-(2-Bromo-1-methoxy-ethoxymethyl)-3-methoxy-5-vinyl-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: 89.0%

1,2-dibromoethyl methyl ether (41824-88-8) + 5-Hydroxymethyl-3-methoxy-5-vinyl-cyclohex-2-enone (66556-43-2) → 5-(2-Bromo-1-methoxy-ethoxymethyl)-3-methoxy-5-vinyl-cyclohex-2-enone (66556-44-3)

Guidance literature:

With N,N-dimethyl-aniline; In dichloromethane; for 0.75h; Ambient temperature;

DOI:10.1021/ja00522a057

Reference yield:

5-(2-Bromo-1-methoxy-ethoxymethyl)-3-methoxy-5-vinyl-cyclohex-2-enone (66556-44-3) → (3R,4aR,8aS)-3,7-Dimethoxy-8a-vinyl-4,4a,8,8a-tetrahydro-1H,3H-isochromen-5-one (66556-46-5) + (S)-5-((R)-2-Bromo-1-methoxy-ethoxymethyl)-3-methoxy-5-vinyl-cyclohex-2-enone (66556-44-3)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; hexane; at 0 ℃; Title compound not separated from byproducts;

DOI:10.1021/ja00522a057

Reference yield:

3-Methoxy-5-oxo-1-vinyl-cyclohex-3-enecarboxylic acid ethyl ester (66556-42-1) → 5-(2-Bromo-1-methoxy-ethoxymethyl)-3-methoxy-5-vinyl-cyclohex-2-enone (66556-44-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) i-Pr₂NLi, 2.) LiAlH₄ / 1.) THF, hexane, 0 deg C, 10 min, 2.) 0 deg C, 10 min

2: 89 percent / N,N-dimethylaniline / CH₂Cl₂ / 0.75 h / Ambient temperature

With lithium aluminium tetrahydride; N,N-dimethyl-aniline; lithium diisopropyl amide; In dichloromethane;

DOI:10.1021/ja00522a057

upstream raw materials:

1,2-dibromoethyl methyl ether

5-Hydroxymethyl-3-methoxy-5-vinyl-cyclohex-2-enone

3-Hydroxy-5-oxo-1-vinyl-cyclohex-3-enecarboxylic acid ethyl ester

3-Methoxy-5-oxo-1-vinyl-cyclohex-3-enecarboxylic acid ethyl ester

Downstream raw materials:

5-(2-Iodo-1-methoxy-ethoxymethyl)-3-methoxy-5-vinyl-cyclohex-2-enone

(3R,4aR,8aS)-3,7-Dimethoxy-8a-vinyl-4,4a,8,8a-tetrahydro-1H,3H-isochromen-5-one

5-Hydroxymethyl-3-methoxy-5-vinyl-cyclohex-2-enone

(S)-5-((R)-2-Iodo-1-methoxy-ethoxymethyl)-3-methoxy-5-vinyl-cyclohex-2-enone