6-[2-(tert-butyldimethylsilanoxy)-6-methoxyphenyl]-2,2,4-trimethyl-1,2-dihydroquinoline-5-carboxylic acid methyl ester

Base Information

• Chemical Name: 6-[2-(tert-butyldimethylsilanoxy)-6-methoxyphenyl]-2,2,4-trimethyl-1,2-dihydroquinoline-5-carboxylic acid methyl ester
• CAS No.: 430436-49-0
• Molecular Formula: C₂₇H₃₇NO₄Si
• Molecular Weight: 467.681
• Mol file: 430436-49-0.mol

Synonyms:6-[2-(tert-butyldimethylsilanoxy)-6-methoxyphenyl]-2,2,4-trimethyl-1,2-dihydroquinoline-5-carboxylic acid methyl ester

Chemical Property of 6-[2-(tert-butyldimethylsilanoxy)-6-methoxyphenyl]-2,2,4-trimethyl-1,2-dihydroquinoline-5-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-[2-(tert-butyldimethylsilanoxy)-6-methoxyphenyl]-2,2,4-trimethyl-1,2-dihydroquinoline-5-carboxylic acid methyl ester

There total 1 articles about 6-[2-(tert-butyldimethylsilanoxy)-6-methoxyphenyl]-2,2,4-trimethyl-1,2-dihydroquinoline-5-carboxylic 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:

sodium methylate (124-41-4) + tert-butyldimethylsilyl chloride (18162-48-6) + 2,5-dihydro-10-methoxy-5-oxo-2,2,4-trimethyl-1H-[1]benzopyrano [3,4-f]quinoline (239070-97-4) → 6-[2-(tert-butyldimethylsilanoxy)-6-methoxyphenyl]-2,2,4-trimethyl-1,2-dihydroquinoline-5-carboxylic acid methyl ester (430436-49-0)

Guidance literature:

sodium methylate; 2,5-dihydro-10-methoxy-5-oxo-2,2,4-trimethyl-1H-[1]benzopyrano [3,4-f]quinoline; In tetrahydrofuran; at 0 - 20 ℃;

tert-butyldimethylsilyl chloride; In tetrahydrofuran; at 40 ℃; for 0.5h; Further stages.;

DOI:10.1021/ja0171198

Reference yield:

6-[2-(tert-butyldimethylsilanoxy)-6-methoxyphenyl]-2,2,4-trimethyl-1,2-dihydroquinoline-5-carboxylic acid methyl ester (430436-49-0) → {6-[2-(tert-butyldimethylsilanoxy)-6-methoxyphenyl]-2,2,4-trimethyl-1,2-dihydroxyquinolin-5-yl}methanol (430436-50-3)

Guidance literature:

With diisobutylaluminium hydride; In n-heptane; dichloromethane; at -45 - -40 ℃;

DOI:10.1021/ja0171198

Reference yield:

6-[2-(tert-butyldimethylsilanoxy)-6-methoxyphenyl]-2,2,4-trimethyl-1,2-dihydroquinoline-5-carboxylic acid methyl ester (430436-49-0) → 2-[5-(buta-1,3-dienyl)-2,2,4-trimethyl-1,2-dihydroquinolin-6-yl]-3-methoxyphenol

Guidance literature:

Multi-step reaction with 5 steps

1.1: DIBAL / CH₂Cl₂; heptane / -45 - -40 °C

2.1: 4.8 g / 2-iodoxybenzoic acid / 1-methyl-pyrrolidin-2-one / 2 h / 20 °C

3.1: (+)-DIP-Cl / diethyl ether / 2 h / -78 °C

3.2: diethyl ether / -77 °C

4.1: TBAF / tetrahydrofuran / 2 h / 20 °C

5.1: DIAD; PPh₃ / tetrahydrofuran / 20 °C

With di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; triphenylphosphine; B-chlorodiisopinocampheylborane; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; diethyl ether; n-heptane; dichloromethane; 5.1: Mitsunobu reaction;

DOI:10.1021/ja0171198

upstream raw materials:

sodium methylate

tert-butyldimethylsilyl chloride

2,5-dihydro-10-methoxy-5-oxo-2,2,4-trimethyl-1H-[1]benzopyrano [3,4-f]quinoline

Downstream raw materials:

{6-[2-(tert-butyldimethylsilanoxy)-6-methoxyphenyl]-2,2,4-trimethyl-1,2-dihydroxyquinolin-5-yl}methanol

2-[5-(1-hydroxy-but-3-enyl)-2,2,4-trimethyl-1,2-dihydroquinolin-6-yl]-3-methoxyphenol

5-[1-(tert-butyldimethylsilanyloxy)but-3-enyl]-6-[2-(tert-butyldimethylsilanyloxy)-6-methoxyphenyl]-2,2,4-trimethyl-1,2-dihydroquinoline

2-[5-(1-hydroxy-but-3-enyl)-2,2,4-trimethyl-1,2-dihydroquinolin-6-yl]-3-methoxyphenol