7-{2''-[(tert-butyldiphenylsiloxy)methyl]allyloxy}-6-allyl-5-hydroxy-2-methyl-4H-chromen-4-one

Base Information

• Chemical Name: 7-{2''-[(tert-butyldiphenylsiloxy)methyl]allyloxy}-6-allyl-5-hydroxy-2-methyl-4H-chromen-4-one
• CAS No.: 1203490-48-5
• Molecular Formula: C₃₃H₃₆O₅Si
• Molecular Weight: 540.731
• Mol file: 1203490-48-5.mol

Synonyms:7-{2''-[(tert-butyldiphenylsiloxy)methyl]allyloxy}-6-allyl-5-hydroxy-2-methyl-4H-chromen-4-one

Chemical Property of 7-{2''-[(tert-butyldiphenylsiloxy)methyl]allyloxy}-6-allyl-5-hydroxy-2-methyl-4H-chromen-4-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-{2''-[(tert-butyldiphenylsiloxy)methyl]allyloxy}-6-allyl-5-hydroxy-2-methyl-4H-chromen-4-one

There total 7 articles about 7-{2''-[(tert-butyldiphenylsiloxy)methyl]allyloxy}-6-allyl-5-hydroxy-2-methyl-4H-chromen-4-one 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%

{[2-(bromomethyl)prop-2-en-1-yl]oxy}(tert-butyl)diphenylsilane (913253-34-6) + 6-allyl-5,7-dihydroxy-2-methyl-4H-chromen-4-one (54102-21-5) → 7-{2''-[(tert-butyldiphenylsiloxy)methyl]allyloxy}-6-allyl-5-hydroxy-2-methyl-4H-chromen-4-one (1203490-48-5)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 5h; Inert atmosphere;

DOI:10.1021/acs.jnatprod.0c00587

Reference yield: 45.0%

{[2-(bromomethyl)prop-2-en-1-yl]oxy}(tert-butyl)diphenylsilane (913253-34-6) + 7-allyloxy-5-hydroxy-2-methyl-4H-chromen-4-one (16639-46-6) → 7-{2''-[(tert-butyldiphenylsiloxy)methyl]allyloxy}-8-allyl-5-hydroxy-2-methyl-4H-chromen-4-one (1203490-49-6) + 7-{2''-[(tert-butyldiphenylsiloxy)methyl]allyloxy}-6-allyl-5-hydroxy-2-methyl-4H-chromen-4-one (1203490-48-5)

Guidance literature:

7-allyloxy-5-hydroxy-2-methyl-4H-chromen-4-one; In N,N-dimethyl-formamide; at 220 ℃; for 1.5h; Microwave irradiation;

{[2-(bromomethyl)prop-2-en-1-yl]oxy}(tert-butyl)diphenylsilane; With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 5h; regioselective reaction; Inert atmosphere;

DOI:10.1021/jo902117e

Reference yield:

2,4,6-trihydroxyacetophenone (480-66-0,67471-34-5) → 7-{2''-[(tert-butyldiphenylsiloxy)methyl]allyloxy}-6-allyl-5-hydroxy-2-methyl-4H-chromen-4-one (1203490-48-5)

Guidance literature:

Multi-step reaction with 6 steps

1: pyridine / 4 h / 20 °C

2: potassium carbonate / acetonitrile / 2 h / Reflux

3: water; potassium carbonate / acetonitrile; methanol / 3 h / Reflux

4: potassium carbonate / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere

5: N,N-diethylaniline / 12 h / 220 °C

6: potassium carbonate / N,N-dimethyl-formamide / 5 h / 20 °C / Inert atmosphere

With pyridine; water; potassium carbonate; N,N-diethylaniline; In methanol; N,N-dimethyl-formamide; acetonitrile; 2: |Kostanecki-Robinson Reaction / 4: |Williamson Ether Synthesis / 5: |Claisen Rearrangement;

DOI:10.1021/acs.jnatprod.0c00587

upstream raw materials:

{[2-(bromomethyl)prop-2-en-1-yl]oxy}(tert-butyl)diphenylsilane

6-allyl-5,7-dihydroxy-2-methyl-4H-chromen-4-one

7-allyloxy-5-hydroxy-2-methyl-4H-chromen-4-one

2,4,6-trihydroxyacetophenone

Downstream raw materials:

8-(tert-butyldiphenylsiloxy)methyl-5-hydroxy-2-methyl-6,9-dihydro-4H-oxepino[3,2-g]chromen-4-one

Ptaeroxylinol