[E,(-)]-3-(4-Hydroxyphenyl)propenoic acid 1-(2,3-dihydro-7-oxo-7H-furo[3,2-g][1]benzopyran-2-yl)-1-methylethyl ester

Base Information

• Chemical Name: [E,(-)]-3-(4-Hydroxyphenyl)propenoic acid 1-(2,3-dihydro-7-oxo-7H-furo[3,2-g][1]benzopyran-2-yl)-1-methylethyl ester
• CAS No.: 53106-45-9
• Molecular Formula: C₂₃H₂₀O₆
• Molecular Weight: 392.408
• Mol file: 53106-45-9.mol

Synonyms:2-Propenoicacid, 3-(4-hydroxyphenyl)-, 1-(2,3-dihydro-7-oxo-7H-furo[3,2-g][1]benzopyran-2-yl)-1-methylethylester, (E)-; 7H-Furo[3,2-g][1]benzopyran, 2-propenoic acid deriv.; Secorin

Chemical Property of [E,(-)]-3-(4-Hydroxyphenyl)propenoic acid 1-(2,3-dihydro-7-oxo-7H-furo[3,2-g][1]benzopyran-2-yl)-1-methylethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [E,(-)]-3-(4-Hydroxyphenyl)propenoic acid 1-(2,3-dihydro-7-oxo-7H-furo[3,2-g][1]benzopyran-2-yl)-1-methylethyl ester

There total 8 articles about [E,(-)]-3-(4-Hydroxyphenyl)propenoic acid 1-(2,3-dihydro-7-oxo-7H-furo[3,2-g][1]benzopyran-2-yl)-1-methylethyl ester 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:

C29H34O6Si → secorin (53106-45-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃; for 0.25h;

DOI:10.1016/j.bmcl.2018.06.018

Reference yield:

7-hydroxy-2H-chromen-2-one (93-35-6) → secorin (53106-45-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 1,8-diazabicyclo[5.4.0]undec-7-ene; copper(II) choride dihydrate / acetonitrile / 18 h / 0 °C

2: hydrogen; quinoline / ethyl acetate / 4 h / 20 °C

3: water / 2.5 h / 75 °C

4: 3-chloro-benzenecarboperoxoic acid; sodium hydrogencarbonate / chloroform / 3 h / 0 °C

5: potassium carbonate / dichloromethane / 17 h / 50 °C

6: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.25 h / 0 - 20 °C

With quinoline; copper(II) choride dihydrate; tetrabutyl ammonium fluoride; water; hydrogen; sodium hydrogencarbonate; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; chloroform; ethyl acetate; acetonitrile; 3: |Claisen Rearrangement;

DOI:10.1016/j.bmcl.2018.06.018

Reference yield:

(E)-3-(4'-((tert-butyldimethylsilyl)oxy)phenyl)acrylic acid (141222-28-8) → secorin (53106-45-9)

Guidance literature:

Multi-step reaction with 3 steps

1: thionyl chloride / dichloromethane / 5 h / 0 - 60 °C

2: potassium carbonate / dichloromethane / 17 h / 50 °C

3: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.25 h / 0 - 20 °C

With thionyl chloride; tetrabutyl ammonium fluoride; potassium carbonate; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.bmcl.2018.06.018

upstream raw materials:

7-hydroxy-2H-chromen-2-one

(E)-3-(4'-((tert-butyldimethylsilyl)oxy)phenyl)acrylic acid

7-((2-methylbut-3-yn-2-yl)oxy)-2H-chromen-2-one

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