(4R)-4-(3,4-dimethoxyphenyl)-4-(2-methanesulfonyloxyethyl)cyclohex-2-enole

Base Information

• Chemical Name: (4R)-4-(3,4-dimethoxyphenyl)-4-(2-methanesulfonyloxyethyl)cyclohex-2-enole
• CAS No.: 321351-52-4
• Molecular Formula: C₁₇H₂₄O₆S
• Molecular Weight: 356.44
• Mol file: 321351-52-4.mol

Synonyms:(4R)-4-(3,4-dimethoxyphenyl)-4-(2-methanesulfonyloxyethyl)cyclohex-2-enole

Chemical Property of (4R)-4-(3,4-dimethoxyphenyl)-4-(2-methanesulfonyloxyethyl)cyclohex-2-enole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R)-4-(3,4-dimethoxyphenyl)-4-(2-methanesulfonyloxyethyl)cyclohex-2-enole

There total 9 articles about (4R)-4-(3,4-dimethoxyphenyl)-4-(2-methanesulfonyloxyethyl)cyclohex-2-enole 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: 84.0%

methanesulfonyl chloride (124-63-0) + (4R)-4-(3,4-dimethoxyphenyl)-4-(2-hydroxyethyl)cyclohex-2-enole (321351-51-3) → (4R)-4-(3,4-dimethoxyphenyl)-4-(2-methanesulfonyloxyethyl)cyclohex-2-enole (321351-52-4)

Guidance literature:

In diethyl ether; at 0 ℃; for 1h;

DOI:10.1021/jo001237g

Reference yield:

4-Bromoveratrole (2859-78-1) → (4R)-4-(3,4-dimethoxyphenyl)-4-(2-methanesulfonyloxyethyl)cyclohex-2-enole (321351-52-4)

Guidance literature:

Multi-step reaction with 9 steps

1.1: Mg / tetrahydrofuran

1.2: 94 percent / CuBr-Me₂S; Me₂S / tetrahydrofuran / 0.17 h / -15 °C

2.1: 96 percent / 30percent H₂O₂; LiOH*H₂O / H₂O; tetrahydrofuran / 2 h / 0 °C

3.1: 89 percent / LiAlH₄ / tetrahydrofuran / 1 h / Heating

4.1: NaH / dimethylformamide / 0.5 h / 20 °C

4.2: 84 percent / 17 h / 20 °C

5.1: 85 percent / KHMDS / diethyl ether; toluene / 17 h / 20 °C

6.1: O₃ / CH₂Cl₂ / -78 °C

6.2: PPh₃ / 17 h / -78 - 20 °C

6.3: 83 percent / p-TsOH*H₂O / benzene / 4 h / Heating

7.1: 87 percent / LiAlH₄ / tetrahydrofuran / 0.33 h / 20 °C

8.1: 86 percent / liqud NH₃; Na / tetrahydrofuran / 0.5 h / -78 °C

9.1: 84 percent / diethyl ether / 1 h / 0 °C

With lithium hydroxide; lithium aluminium tetrahydride; ammonia; sodium; potassium hexamethylsilazane; sodium hydride; ozone; magnesium; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo001237g

Reference yield:

(3R)-7-chloro-3-(3,4-dimethoxyphenyl)-6-methylhept-6-en-1-ol (321351-46-6) → (4R)-4-(3,4-dimethoxyphenyl)-4-(2-methanesulfonyloxyethyl)cyclohex-2-enole (321351-52-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: NaH / dimethylformamide / 0.5 h / 20 °C

1.2: 84 percent / 17 h / 20 °C

2.1: 85 percent / KHMDS / diethyl ether; toluene / 17 h / 20 °C

3.1: O₃ / CH₂Cl₂ / -78 °C

3.2: PPh₃ / 17 h / -78 - 20 °C

3.3: 83 percent / p-TsOH*H₂O / benzene / 4 h / Heating

4.1: 87 percent / LiAlH₄ / tetrahydrofuran / 0.33 h / 20 °C

5.1: 86 percent / liqud NH₃; Na / tetrahydrofuran / 0.5 h / -78 °C

6.1: 84 percent / diethyl ether / 1 h / 0 °C

With lithium aluminium tetrahydride; ammonia; sodium; potassium hexamethylsilazane; sodium hydride; ozone; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo001237g

upstream raw materials:

methanesulfonyl chloride

(4R)-4-(3,4-dimethoxyphenyl)-4-(2-hydroxyethyl)cyclohex-2-enole

4-Bromoveratrole

(3R)-7-chloro-3-(3,4-dimethoxyphenyl)-6-methylhept-6-en-1-ol

Downstream raw materials:

(-)-mesembrine