Reaction #8910

Reaction equation

1-chloropinacolone

product

6-(2-Chlorophenyl)-5-(4-chlorophenyl)-3-formyl-2-pyridone

1-chloropinacolone

Cs2CO3

Cs2CO3

→

title compound

1-[6-(2-Chlorophenyl)-5-(4-chlorophenyl)furo[2,3-b]pyridin-2-yl]-2,2-dimethylpropan-1-one

Solvents

Et2O

Conditions

Workup

1. 1
   workup.WAITthe stirring was continued for another 1 h
2. 2
   TemperatureThe solution was cooled
3. 3
   Washwashed with water, brine
4. 4
   Otherdried
5. 5
   Concentrationconcentrated
6. 6
   OtherThe residue was purified on a prep TLC plate

Procedure

To a solution of 0.38 g of the product of Step A dissolved in 3 mL of DW, was added 0.14 mL (1.07 mmol) of 1-chloropinacolone and 0.65 g of Cs2CO3. After stirring for 2 h, another 0.05 mL (0.38 mmol) of 1-chloropinacolone was added and the stirring was continued for another 1 h. Additional 0.325 g (1 mmol) of Cs2CO3 was added and the solution was heated in a 60° C. bath for 3 h. The solution was cooled, diluted with Et2O, washed with water, brine, dried and concentrated. The residue was purified on a prep TLC plate using 20% EtOAc/hexane as eluant to afford the title compound. HPLC/MS: 424 (M+1), 426 (M+3); Rt=4.49 min.

Source