carbonic acid tert-butyl ester 2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-7-methoxy-4-oxo-chroman-5-yl ester

Base Information

• Chemical Name: carbonic acid tert-butyl ester 2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-7-methoxy-4-oxo-chroman-5-yl ester
• CAS No.: 895918-10-2
• Molecular Formula: C₂₇H₃₆O₇Si
• Molecular Weight: 500.664
• Mol file: 895918-10-2.mol

Synonyms:carbonic acid tert-butyl ester 2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-7-methoxy-4-oxo-chroman-5-yl ester

Chemical Property of carbonic acid tert-butyl ester 2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-7-methoxy-4-oxo-chroman-5-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of carbonic acid tert-butyl ester 2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-7-methoxy-4-oxo-chroman-5-yl ester

There total 7 articles about carbonic acid tert-butyl ester 2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-7-methoxy-4-oxo-chroman-5-yl 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: 75.0%

2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-5-hydroxy-7-methoxy-chroman-4-one (895918-19-1) + di-tert-butyl dicarbonate (24424-99-5) → carbonic acid tert-butyl ester 2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-7-methoxy-4-oxo-chroman-5-yl ester (895918-10-2)

Guidance literature:

With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/j.tet.2006.01.109

Reference yield:

tri-tert-butyl (2-formylbenzene-1,3,5-triyl)tricarbonate (895918-06-6) → carbonic acid tert-butyl ester 2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-7-methoxy-4-oxo-chroman-5-yl ester (895918-10-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: magnesium bromide dietherate / diethyl ether

1.2: 45 percent / lithium aluminum hydride / diethyl ether / 3 h / -78 - 20 °C

2.1: 88 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 20 °C

3.1: 82 percent / zinc bromide / CH₂Cl₂ / 6 h / 20 °C

4.1: Na₂CO₃ / dimethylformamide / 20 °C

5.1: 2,6-lutidine / tetrahydrofuran / 4 h / 20 °C

6.1: 75 percent / 4-(dimethylamino)pyridine; Et(i-Pr)2N / CH₂Cl₂ / 1 h / 20 °C

With 2,6-dimethylpyridine; dmap; sodium carbonate; magnesium dibromide etherate; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc dibromide; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2006.01.109

Reference yield:

carbonic acid 5-tert-butoxycarbonyloxy-2-(4-tert-butoxy-phenyl)-chroman-7-yl ester tert-butyl ester (895918-07-7) → carbonic acid tert-butyl ester 2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-7-methoxy-4-oxo-chroman-5-yl ester (895918-10-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 88 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 20 °C

2: 82 percent / zinc bromide / CH₂Cl₂ / 6 h / 20 °C

3: Na₂CO₃ / dimethylformamide / 20 °C

4: 2,6-lutidine / tetrahydrofuran / 4 h / 20 °C

5: 75 percent / 4-(dimethylamino)pyridine; Et(i-Pr)2N / CH₂Cl₂ / 1 h / 20 °C

With 2,6-dimethylpyridine; dmap; sodium carbonate; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc dibromide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2006.01.109

upstream raw materials:

2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-5-hydroxy-7-methoxy-chroman-4-one

di-tert-butyl dicarbonate

tri-tert-butyl (2-formylbenzene-1,3,5-triyl)tricarbonate

carbonic acid 5-tert-butoxycarbonyloxy-2-(4-tert-butoxy-phenyl)-chroman-7-yl ester tert-butyl ester