2-[(2E,6E)-8-(tert-Butyl-dimethyl-silanyloxy)-2,6-dimethyl-octa-2,6-dienylamino]-benzoic acid methyl ester

Base Information

• Chemical Name: 2-[(2E,6E)-8-(tert-Butyl-dimethyl-silanyloxy)-2,6-dimethyl-octa-2,6-dienylamino]-benzoic acid methyl ester
• CAS No.: 798573-58-7
• Molecular Formula: C₂₄H₃₉NO₃Si
• Molecular Weight: 417.664
• Mol file: 798573-58-7.mol

Synonyms:2-[(2E,6E)-8-(tert-Butyl-dimethyl-silanyloxy)-2,6-dimethyl-octa-2,6-dienylamino]-benzoic acid methyl ester

Chemical Property of 2-[(2E,6E)-8-(tert-Butyl-dimethyl-silanyloxy)-2,6-dimethyl-octa-2,6-dienylamino]-benzoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(2E,6E)-8-(tert-Butyl-dimethyl-silanyloxy)-2,6-dimethyl-octa-2,6-dienylamino]-benzoic acid methyl ester

There total 3 articles about 2-[(2E,6E)-8-(tert-Butyl-dimethyl-silanyloxy)-2,6-dimethyl-octa-2,6-dienylamino]-benzoic acid methyl 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: 89.0%

anthranilic acid methyl ester hydrochloride (13516-02-4) + (2E,6E)-8-(tert-butyldimethylsilyloxy)-2,6-dimethylocta-2,6-dienal (138842-85-0) → 2-[(2E,6E)-8-(tert-Butyl-dimethyl-silanyloxy)-2,6-dimethyl-octa-2,6-dienylamino]-benzoic acid methyl ester (798573-58-7)

Guidance literature:

anthranilic acid methyl ester hydrochloride; (2E,6E)-8-(tert-butyldimethylsilyloxy)-2,6-dimethylocta-2,6-dienal; With acetic acid; In 1,2-dichloro-ethane; at 20 ℃; for 0.0833333h;

With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20 ℃; for 2.7h;

DOI:10.1021/jo049101w

Reference yield:

(2E,6E)-3,7-dimethyl-8-oxoocta-2,6-dien-1-yl acetate (37905-02-5) → 2-[(2E,6E)-8-(tert-Butyl-dimethyl-silanyloxy)-2,6-dimethyl-octa-2,6-dienylamino]-benzoic acid methyl ester (798573-58-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: K₂CO₃ / methanol / 2.5 h / 20 °C

2.1: 3.89 g / i-Pr₂NEt / tetrahydrofuran / 2 h / 0 °C

3.1: acetic acid / 1,2-dichloro-ethane / 0.08 h / 20 °C

3.2: 89 percent / NaBH(OAc)3 / 1,2-dichloro-ethane / 2.7 h / 20 °C

With potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; 1,2-dichloro-ethane;

DOI:10.1021/jo049101w

Reference yield:

(2E,6E)-8-hydroxy-2,6-dimethylocta-2,6-dienal (38290-51-6) → 2-[(2E,6E)-8-(tert-Butyl-dimethyl-silanyloxy)-2,6-dimethyl-octa-2,6-dienylamino]-benzoic acid methyl ester (798573-58-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 3.89 g / i-Pr₂NEt / tetrahydrofuran / 2 h / 0 °C

2.1: acetic acid / 1,2-dichloro-ethane / 0.08 h / 20 °C

2.2: 89 percent / NaBH(OAc)3 / 1,2-dichloro-ethane / 2.7 h / 20 °C

With acetic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,2-dichloro-ethane;

DOI:10.1021/jo049101w

upstream raw materials:

anthranilic acid methyl ester hydrochloride

(2E,6E)-8-(tert-butyldimethylsilyloxy)-2,6-dimethylocta-2,6-dienal

(2E,6E)-3,7-dimethyl-8-oxoocta-2,6-dien-1-yl acetate

(2E,6E)-8-hydroxy-2,6-dimethylocta-2,6-dienal

Downstream raw materials:

2-((2E,6E)-8-Chloro-2,6-dimethyl-octa-2,6-dienylamino)-benzoic acid methyl ester

methyl 2-((2E,6E)-8-hydroxy-2,6-dimethyl-octa-2,6-dienylamino)benzoate