ChemicalBook CAS DataBase List 4H-Pyran-4-one,3-methoxy-(6CI,7CI,8CI,9CI)

4H-Pyran-4-one,3-methoxy-(6CI,7CI,8CI,9CI) synthesis

5synthesis methods

Product Name:4H-Pyran-4-one,3-methoxy-(6CI,7CI,8CI,9CI)
CAS Number:1193-64-2
Molecular formula:C6H6O3
Molecular Weight:126.11

4H-Pyran-2-carboxylic acid, 5-methoxy-4-oxo-

1199-60-6
19 suppliers
$32.00/100mg

4H-Pyran-4-one,3-methoxy-(6CI,7CI,8CI,9CI)

1193-64-2
16 suppliers
inquiry

Yield:1193-64-2 45%

Reaction Conditions:

in 1-methyl-pyrrolidin-2-one for 4 h;Reflux;

Steps:

3 3-Methoxy-4H-pyran-4-one (14a)
5-Methoxy-4-oxo-4H-pyran-2-carboxylic acid (13a) (34.00 g, 200 mmol) and 1-methyl-2- pyrrolidinone (500 mL) were refluxed for 4 h.
The solvent was removed azeotropically with N,N-dimethylformamide (500 mL) in high vacuum.
The residue was extracted into dichloromethane and washed with 5% aqueous sodium hydroxide (3 * 270 mL).
The organic layer was dried over Na₂SO₄, concentrated and recrystallized from toluene to give the yellow solid (14a) (11.32 g, 45%). 1H NMR (400 MHz, DMSO-d6) d: 7.53 (s, 1H), 7.45 (s,1H), 3.66 (s, 3H), 3.25 (s, 2H), 2.14 (s, 6H); 13C NMR (100 MHz,DMSO-d6) d: 164.5, 148.1, 134.7, 122.6, 120.7, 56.0, 55.0, 44.9.

References:

Xie, Yuan-Yuan;Lu, Zidong;Kong, Xiao-Le;Zhou, Tao;Bansal, Sukhi;Hider, Robert [European Journal of Medicinal Chemistry,2016,vol. 115,p. 132 - 140]

FullText

501-30-4 Synthesis