N,N-diethyl-3-methoxy-5-(methoxymethoxy)-4-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]benzamide

Base Information

• Chemical Name: N,N-diethyl-3-methoxy-5-(methoxymethoxy)-4-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]benzamide
• CAS No.: 1422953-21-6
• Molecular Formula: C₂₉H₄₅NO₄
• Molecular Weight: 471.681
• Mol file: 1422953-21-6.mol

Synonyms:N,N-diethyl-3-methoxy-5-(methoxymethoxy)-4-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]benzamide

Chemical Property of N,N-diethyl-3-methoxy-5-(methoxymethoxy)-4-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]benzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N,N-diethyl-3-methoxy-5-(methoxymethoxy)-4-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]benzamide

There total 2 articles about N,N-diethyl-3-methoxy-5-(methoxymethoxy)-4-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]benzamide 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: 70.0%

4-bromo-N,N-diethyl-3-methoxy-5-(methoxymethoxy)benzamide (1422953-20-5) + (E,E)-Farnesyltri-n-butylstannane → N,N-diethyl-3-methoxy-5-(methoxymethoxy)-4-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]benzamide (1422953-21-6)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; cesium fluoride; In N,N-dimethyl-formamide; at 90 ℃; for 36h; Inert atmosphere;

DOI:10.1055/s-0032-1317544

Reference yield:

methyl 4-bromo-3-methoxy-5-(methoxymethoxy)benzoate (1422953-18-1) → N,N-diethyl-3-methoxy-5-(methoxymethoxy)-4-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]benzamide (1422953-21-6)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium hydroxide / water; methanol / 8 h / 25 °C

2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 12 h / 0 - 25 °C / Inert atmosphere

3: bis-triphenylphosphine-palladium(II) chloride; cesium fluoride / N,N-dimethyl-formamide / 36 h / 90 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; cesium fluoride; potassium hydroxide; In methanol; water; N,N-dimethyl-formamide; 3: |Stille Cross Coupling;

DOI:10.1055/s-0032-1317544

Reference yield: 88.0%

N,N-diethyl-3-methoxy-5-(methoxymethoxy)-4-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]benzamide (1422953-21-6) → N,N-diethyl-3-hydroxy-5-methoxy-4-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]benzamide (1422953-22-7)

Guidance literature:

With camphor-10-sulfonic acid; In methanol; at 25 ℃; for 12h; Inert atmosphere;

DOI:10.1055/s-0032-1317544

upstream raw materials:

4-bromo-N,N-diethyl-3-methoxy-5-(methoxymethoxy)benzamide

methyl 4-bromo-3-methoxy-5-(methoxymethoxy)benzoate

Downstream raw materials:

N,N-diethyl-3-hydroxy-5-methoxy-4-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]benzamide