Naphtho[2,3-c]furan-1(3H)-one, 7-hydroxy-3-methyl-4-phenyl-

Base Information

• Chemical Name: Naphtho[2,3-c]furan-1(3H)-one, 7-hydroxy-3-methyl-4-phenyl-
• CAS No.: 145127-77-1
• Molecular Formula: C19H14O3
• Molecular Weight: 290.318
• Mol file: 145127-77-1.mol

Synonyms:

Chemical Property of Naphtho[2,3-c]furan-1(3H)-one, 7-hydroxy-3-methyl-4-phenyl-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Naphtho[2,3-c]furan-1(3H)-one, 7-hydroxy-3-methyl-4-phenyl-

There total 12 articles about Naphtho[2,3-c]furan-1(3H)-one, 7-hydroxy-3-methyl-4-phenyl- 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: 83.0%

7-Benzyloxy-3-methyl-4-phenyl-3H-naphtho[2,3-c]furan-1-one (145127-76-0) → 7-Hydroxy-3-methyl-4-phenyl-3H-naphtho[2,3-c]furan-1-one (145127-77-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 48h; Ambient temperature;

DOI:10.1021/jm960301c

Reference yield:

5-(benzyloxy)-2-bromobenzaldehyde dimethylacetal (81418-49-7) → 7-Hydroxy-3-methyl-4-phenyl-3H-naphtho[2,3-c]furan-1-one (145127-77-1)

Guidance literature:

Multi-step reaction with 12 steps

1: 1.) n-BuLi / 1.) THF, hexane, -70 deg C, 15 min, 2.) THF, hexane, from -70 to 10 deg C

2: camphorsulfonic acid / toluene / 24 h / Heating

3: 29 percent / LiAlH₄ / tetrahydrofuran / 2.5 h / Heating

4: 73 percent / imidazole / tetrahydrofuran / 1 h / Ambient temperature

5: 92 percent / pyridinium chlorochromate, molecular sieves / CH₂Cl₂ / 1 h / Ambient temperature

6: 98 percent / tetrahydrofuran / 0.17 h / -78 °C

7: pyridine, 4-(dimethylamino)pyridine / 2 h / Ambient temperature

8: Bu₄NF, acetic acid / tetrahydrofuran / 2 h / 0 °C

9: 91 percent / KMnO₄, aq. phoshate buffer / 2-methyl-propan-2-ol; H₂O / 3 h / Ambient temperature

10: 100 percent / MeONa / methanol / 24 h / Ambient temperature

11: 100 percent / 6N aq. HCl / ethyl acetate / 0.33 h / Ambient temperature

12: 83 percent / H₂ / 10percent Pd/C / ethyl acetate / 48 h / Ambient temperature

With pyridine; 1H-imidazole; hydrogenchloride; dmap; potassium permanganate; lithium aluminium tetrahydride; n-butyllithium; molecular sieve; phoshate buffer; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; acetic acid; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; toluene; tert-butyl alcohol;

DOI:10.1021/jm960301c

Reference yield:

7-benzyloxy-2,3-bis(hydroxymethyl)-4-phenylnaphthalene (144801-46-7) → 7-Hydroxy-3-methyl-4-phenyl-3H-naphtho[2,3-c]furan-1-one (145127-77-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 73 percent / imidazole / tetrahydrofuran / 1 h / Ambient temperature

2: 92 percent / pyridinium chlorochromate, molecular sieves / CH₂Cl₂ / 1 h / Ambient temperature

3: 98 percent / tetrahydrofuran / 0.17 h / -78 °C

4: pyridine, 4-(dimethylamino)pyridine / 2 h / Ambient temperature

5: Bu₄NF, acetic acid / tetrahydrofuran / 2 h / 0 °C

6: 91 percent / KMnO₄, aq. phoshate buffer / 2-methyl-propan-2-ol; H₂O / 3 h / Ambient temperature

7: 100 percent / MeONa / methanol / 24 h / Ambient temperature

8: 100 percent / 6N aq. HCl / ethyl acetate / 0.33 h / Ambient temperature

9: 83 percent / H₂ / 10percent Pd/C / ethyl acetate / 48 h / Ambient temperature

With pyridine; 1H-imidazole; hydrogenchloride; dmap; potassium permanganate; molecular sieve; phoshate buffer; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; acetic acid; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; tert-butyl alcohol;

DOI:10.1021/jm960301c

upstream raw materials:

7-Benzyloxy-3-methyl-4-phenyl-3H-naphtho[2,3-c]furan-1-one

5-(benzyloxy)-2-bromobenzaldehyde dimethylacetal

7-benzyloxy-2,3-bis(hydroxymethyl)-4-phenylnaphthalene

7-Benzyloxy-4-phenyl-naphtho[2,3-c]furan-1,3-dione

Refernces