4-Azido-3-((Z)-3-methoxycarbonyl-6,7-dimethyl-octa-2,6-dienyl)-benzoic acid ethyl ester

Base Information

• Chemical Name: 4-Azido-3-((Z)-3-methoxycarbonyl-6,7-dimethyl-octa-2,6-dienyl)-benzoic acid ethyl ester
• CAS No.: 134721-36-1
• Molecular Formula: C₂₁H₂₇N₃O₄
• Molecular Weight: 385.463
• Mol file: 134721-36-1.mol

Synonyms:4-Azido-3-((Z)-3-methoxycarbonyl-6,7-dimethyl-octa-2,6-dienyl)-benzoic acid ethyl ester

Chemical Property of 4-Azido-3-((Z)-3-methoxycarbonyl-6,7-dimethyl-octa-2,6-dienyl)-benzoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Azido-3-((Z)-3-methoxycarbonyl-6,7-dimethyl-octa-2,6-dienyl)-benzoic acid ethyl ester

There total 5 articles about 4-Azido-3-((Z)-3-methoxycarbonyl-6,7-dimethyl-octa-2,6-dienyl)-benzoic acid ethyl 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: 63.0%

4-Azido-3-(2-oxo-ethyl)-benzoic acid ethyl ester (134721-34-9) + 2-[Bis-(2,2,2-trifluoro-ethoxy)-phosphoryl]-5,6-dimethyl-hept-5-enoic acid methyl ester (134721-37-2) → 4-Azido-3-((Z)-3-methoxycarbonyl-6,7-dimethyl-octa-2,6-dienyl)-benzoic acid ethyl ester (134721-36-1)

Guidance literature:

With 18-crown-6 ether; potassium hexamethylsilazane; In tetrahydrofuran; at -78 - -40 ℃; for 2.5h;

DOI:10.1016/0040-4020(96)00609-6

Reference yield:

5-bromo-2,3-dimethyl-2-pentene (56312-52-8) → 4-Azido-3-((Z)-3-methoxycarbonyl-6,7-dimethyl-octa-2,6-dienyl)-benzoic acid ethyl ester (134721-36-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaH / 1.) DMSO, hexane, RT, 10 min, 2.) DMSO, hexane, RT, 3 d

2: 63 percent / potassium hexamethyldisilazide, 18-crown-6 / tetrahydrofuran / 2.5 h / -78 - -40 °C

With 18-crown-6 ether; potassium hexamethylsilazane; sodium hydride; In tetrahydrofuran;

DOI:10.1016/0040-4020(96)00609-6

Reference yield:

ethyl 4-amino-3-(2-propenyl)benzoate (59816-84-1) → 4-Azido-3-((Z)-3-methoxycarbonyl-6,7-dimethyl-octa-2,6-dienyl)-benzoic acid ethyl ester (134721-36-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) 12 N aq. HCl, aq. NaNO₂, 2.) aq. NaN₃ / 1.) 0 deg C, 15 min, 2.) 0 deg C, 1 h 45 min

2: aq. OsO₄, N-methylmorpholine N-oxide / acetone / 17 h / Ambient temperature

3: aq. NaIO₄ / tetrahydrofuran / 1 h / Ambient temperature

4: 63 percent / potassium hexamethyldisilazide, 18-crown-6 / tetrahydrofuran / 2.5 h / -78 - -40 °C

With hydrogenchloride; sodium periodate; osmium(VIII) oxide; sodium azide; 18-crown-6 ether; potassium hexamethylsilazane; 4-methylmorpholine N-oxide; sodium nitrite; In tetrahydrofuran; acetone;

DOI:10.1016/0040-4020(96)00609-6

upstream raw materials:

4-Azido-3-(2-oxo-ethyl)-benzoic acid ethyl ester

2-[Bis-(2,2,2-trifluoro-ethoxy)-phosphoryl]-5,6-dimethyl-hept-5-enoic acid methyl ester

5-bromo-2,3-dimethyl-2-pentene

ethyl 4-amino-3-(2-propenyl)benzoate