2-[(Z)-2-(diethylcarbamoyl)vinyl]-5-methoxyphenyl acetate

Base Information

• Chemical Name: 2-[(Z)-2-(diethylcarbamoyl)vinyl]-5-methoxyphenyl acetate
• CAS No.: 300767-60-6
• Molecular Formula: C₁₆H₂₁NO₄
• Molecular Weight: 291.347
• Mol file: 300767-60-6.mol

Synonyms:2-[(Z)-2-(diethylcarbamoyl)vinyl]-5-methoxyphenyl acetate

Chemical Property of 2-[(Z)-2-(diethylcarbamoyl)vinyl]-5-methoxyphenyl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(Z)-2-(diethylcarbamoyl)vinyl]-5-methoxyphenyl acetate

There total 7 articles about 2-[(Z)-2-(diethylcarbamoyl)vinyl]-5-methoxyphenyl acetate 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: 29.0%

diethylamine (109-89-7) + (Z)-3-[2-(acetyloxy)-4-methoxyphenyl]acrylic acid (300767-58-2) → 2-[(Z)-2-(diethylcarbamoyl)vinyl]-5-methoxyphenyl acetate (300767-60-6)

Guidance literature:

(Z)-3-[2-(acetyloxy)-4-methoxyphenyl]acrylic acid; With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; at 0 ℃; for 0.166667h;

diethylamine; With dmap; benzotriazol-1-ol; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1248/cpb.48.1138

Reference yield:

7-methoxycoumarin (531-59-9) → 2-[(Z)-2-(diethylcarbamoyl)vinyl]-5-methoxyphenyl acetate (300767-60-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 39 percent / LAH / diethyl ether / 0.25 h / 0 °C

2.1: 80 percent / DMAP / tetrahydrofuran / 8 h / 0 °C

3.1: 99 percent / DMAP; TEA / CH₂Cl₂ / 1 h / 20 °C

4.1: 100 percent / aq. AcOH / tetrahydrofuran / 4.5 h / 20 °C

5.1: 74 percent / MnO₂ / CH₂Cl₂ / 5 h

6.1: 77 percent / aq. sodium chlorite; sodium phosphate; 30 percent H₂O₂ / acetonitrile / 2 h / 10 °C

7.1: EDC / CH₂Cl₂ / 0.17 h / 0 °C

7.2: 29 percent / DMAP; HOBt / CH₂Cl₂ / 1 h / 20 °C

With dmap; manganese(IV) oxide; sodium chlorite; lithium aluminium tetrahydride; TEA; dihydrogen peroxide; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; sodium phosphate; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile;

DOI:10.1248/cpb.48.1138

Reference yield:

2-[(Z)-3-hydroxy-1-propenyl]-5-methoxyphenol (300767-53-7) → 2-[(Z)-2-(diethylcarbamoyl)vinyl]-5-methoxyphenyl acetate (300767-60-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 80 percent / DMAP / tetrahydrofuran / 8 h / 0 °C

2.1: 99 percent / DMAP; TEA / CH₂Cl₂ / 1 h / 20 °C

3.1: 100 percent / aq. AcOH / tetrahydrofuran / 4.5 h / 20 °C

4.1: 74 percent / MnO₂ / CH₂Cl₂ / 5 h

5.1: 77 percent / aq. sodium chlorite; sodium phosphate; 30 percent H₂O₂ / acetonitrile / 2 h / 10 °C

6.1: EDC / CH₂Cl₂ / 0.17 h / 0 °C

6.2: 29 percent / DMAP; HOBt / CH₂Cl₂ / 1 h / 20 °C

With dmap; manganese(IV) oxide; sodium chlorite; TEA; dihydrogen peroxide; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; sodium phosphate; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1248/cpb.48.1138

upstream raw materials:

diethylamine

(Z)-3-[2-(acetyloxy)-4-methoxyphenyl]acrylic acid

7-methoxycoumarin

2-[(Z)-3-hydroxy-1-propenyl]-5-methoxyphenol

Downstream raw materials:

7-methoxycoumarin

diethylamine

Refernces