ethyl 9,11-di-cis-13,14-dihydro-4-oxoretinoate

Base Information

• Chemical Name: ethyl 9,11-di-cis-13,14-dihydro-4-oxoretinoate
• CAS No.: 879207-49-5
• Molecular Formula: C₂₂H₃₂O₃
• Molecular Weight: 344.494
• Mol file: 879207-49-5.mol

Synonyms:ethyl 9,11-di-cis-13,14-dihydro-4-oxoretinoate

Chemical Property of ethyl 9,11-di-cis-13,14-dihydro-4-oxoretinoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 9,11-di-cis-13,14-dihydro-4-oxoretinoate

There total 5 articles about ethyl 9,11-di-cis-13,14-dihydro-4-oxoretinoate 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:

ethyl 3-formylbutyrate (54998-57-1) + (2E,4E)-<5-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadien-1-yl>triphenylphosphonium bromide (63184-93-0) → ethyl 9,11-di-cis-13,14-dihydro-4-oxoretinoate (879207-49-5) + ethyl 9-cis-13,14-dihydro-4-oxoretinoate (879207-48-4) + ethyl 11-cis-13,14-dihydro-4-oxoretinoate (879207-47-3) + ethyl 13,14-dihydro-4-oxoretinoate (879207-46-2)

Guidance literature:

With 18-crown-6 ether; potassium tert-butylate; In dichloromethane; at -78 - 20 ℃; for 6h;

Reference yield:

3-formyl crotonic acid ethyl ester (41891-38-7) → ethyl 9,11-di-cis-13,14-dihydro-4-oxoretinoate (879207-49-5) + ethyl 9-cis-13,14-dihydro-4-oxoretinoate (879207-48-4) + ethyl 11-cis-13,14-dihydro-4-oxoretinoate (879207-47-3)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen / palladium 10% on activated carbon / methanol / 24 h / 20 °C

2: 18-crown-6 ether; potassium tert-butylate / dichloromethane / 6 h / -78 - 20 °C

With 18-crown-6 ether; potassium tert-butylate; hydrogen; palladium 10% on activated carbon; In methanol; dichloromethane;

Reference yield:

ethyl (+/-)-(2E,4E)-5-[1-(3-[(1,1-dimethylethyl)dimethylsilyloxy]-2,6,6-trimethyl-1-cyclohexen-1-yl)]-3-methyl-2,4-pentadienoate (937391-73-6) → ethyl 9,11-di-cis-13,14-dihydro-4-oxoretinoate (879207-49-5) + ethyl 9-cis-13,14-dihydro-4-oxoretinoate (879207-48-4) + ethyl 11-cis-13,14-dihydro-4-oxoretinoate (879207-47-3)

Guidance literature:

Multi-step reaction with 8 steps

1: lithium aluminium tetrahydride / diethyl ether / 0.5 h / 0 °C

2: dmap / dichloromethane / 2 h / 20 °C

3: tetrabutyl ammonium fluoride / tetrahydrofuran / 16 h / 20 °C

4: manganese(IV) oxide / dichloromethane / 24 h / 20 °C

5: water; potassium carbonate / methanol / 6 h / 20 °C

6: pyridine; phosphorus tribromide / diethyl ether / 1 h / -20 °C

7: toluene / 24 h / 20 °C

8: 18-crown-6 ether; potassium tert-butylate / dichloromethane / 6 h / -78 - 20 °C

With pyridine; dmap; manganese(IV) oxide; lithium aluminium tetrahydride; 18-crown-6 ether; potassium tert-butylate; tetrabutyl ammonium fluoride; water; phosphorus tribromide; potassium carbonate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene;

upstream raw materials:

ethyl 3-formylbutyrate

(2E,4E)-<5-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-2,4-pentadien-1-yl>triphenylphosphonium bromide

ethyl (+/-)-(2E,4E)-5-[1-(3-[(1,1-dimethylethyl)dimethylsilyloxy]-2,6,6-trimethyl-1-cyclohexen-1-yl)]-3-methyl-2,4-pentadienoate

1-(2,6,6-Trimethyl-3-oxo-1-cyclohexen-1-yl)-3-methyl-5-bromo-penta-1,3-diene

Refernces