ChemicalBook CAS DataBase List 6H-dibenzo-(b,d)-pyran-6-one

6H-dibenzo-(b,d)-pyran-6-one synthesis

15synthesis methods

Product Name:6H-dibenzo-(b,d)-pyran-6-one
CAS Number:2005-10-9
Molecular formula:C13H8O2
Molecular Weight:196.2

26260-02-6 Synthesis

26260-02-6
241 suppliers
$8.00/250mg

89466-08-0 Synthesis

89466-08-0
314 suppliers
$5.00/1g

2005-10-9
42 suppliers
$48.00/250mg

Yield: 91%

Reaction Conditions:

with palladium diacetate;potassium carbonate;triphenylphosphine in N,N-dimethyl-formamide at 90; for 3 h;Inert atmosphere;Suzuki-Miyaura Coupling;Reagent/catalyst;Temperature;Solvent;

Steps:

General procedure for the one-pot synthesis of benzo[c]chromen-6-ones:
General procedure: The 2-bromoarylcarboxaldehyde (1 mmol), 2-hydroxyphenylboronic acid (1 mmol), K₂CO₃ (1 mmol.), PPh₃ (0.25 mmol) were taken in a two-necked round bottomed flask and flushed with nitrogen gas. Then 3 mL of DMF was added and degassed with N2. The catalyst Pd(OAc)2 (5 mol%) was added to the reaction mixture and heated at 90 ^°C for 4 h. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, diluted with water and extracted with ethyl acetate (3 × 20 mL). The combined organic layer was dried over Na2SO4 and evaporated under reduced pressure. The crude product was purified by column chromatography using silica gel (60-120 mesh) and hexane/EtOAc as eluent.

References:

Singha, Raju;Roy, Soumyabrata;Nandi, Sukla;Ray, Priyanka;Ray, Jayanta K. [Tetrahedron Letters,2013,vol. 54,# 7,p. 657 - 660] Location in patent:supporting information