4a-(tert-Butoxycarbonyl)-2-phenyl-4a,7,8,8a-tetrahydro-4H-benzopyran-4,7-dione

Base Information

• Chemical Name: 4a-(tert-Butoxycarbonyl)-2-phenyl-4a,7,8,8a-tetrahydro-4H-benzopyran-4,7-dione
• CAS No.: 186424-35-1
• Molecular Formula: C₂₀H₂₀O₅
• Molecular Weight: 340.376

Synonyms:4a-(tert-Butoxycarbonyl)-2-phenyl-4a,7,8,8a-tetrahydro-4H-benzopyran-4,7-dione

Chemical Property of 4a-(tert-Butoxycarbonyl)-2-phenyl-4a,7,8,8a-tetrahydro-4H-benzopyran-4,7-dione

Chemical Property:

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Technology Process of 4a-(tert-Butoxycarbonyl)-2-phenyl-4a,7,8,8a-tetrahydro-4H-benzopyran-4,7-dione

There total 5 articles about 4a-(tert-Butoxycarbonyl)-2-phenyl-4a,7,8,8a-tetrahydro-4H-benzopyran-4,7-dione 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: 78.0%

4a-(tert-Butoxycarbonyl)-5-methoxy-2-phenyl-7-trimethylsilyloxy-4a,5,8,8a-tetrahydro-4H-benzopyran-4-one → 4a-(tert-Butoxycarbonyl)-2-phenyl-4a,7,8,8a-tetrahydro-4H-benzopyran-4,7-dione (186424-35-1)

Guidance literature:

With trifluoroacetic anhydride; In dichloromethane; for 0.5h;

DOI:10.1039/a602245f

Reference yield: 78.0%

(R)-5-Methoxy-4,7-dioxo-2-phenyl-6,7,8,8a-tetrahydro-4H,5H-chromene-4a-carboxylic acid tert-butyl ester → 4a-(tert-Butoxycarbonyl)-2-phenyl-4a,7,8,8a-tetrahydro-4H-benzopyran-4,7-dione (186424-35-1)

Guidance literature:

With trifluoroacetic anhydride; In dichloromethane; for 0.5h;

DOI:10.1039/a602245f

Reference yield:

tert-Butyl 4-oxo-6-phenyl-4H-pyran-3-carboxylate (134653-74-0) → 4a-(tert-Butoxycarbonyl)-2-phenyl-4a,7,8,8a-tetrahydro-4H-benzopyran-4,7-dione (186424-35-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 52 percent / toluene / 6 h / 110 °C

2: 78 percent / TFAA / CH₂Cl₂ / 0.5 h

With trifluoroacetic anhydride; In dichloromethane; toluene;

DOI:10.1039/a602245f

upstream raw materials:

tert-butyl acetoacetate

2-((dimethylamino)methylene)-3-oxobutyric acid tert-butyl ester

tert-Butyl 4-oxo-6-phenyl-4H-pyran-3-carboxylate

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