Reaction #68003

Reaction equation

1-(1,3-dioxolan-2-ylmethyl)-6-isopropylquinolin-2(1H)-one

trifluoroacetic acid

→

(6-isopropyl-2-oxoquinolin-1(2H)-yl)acetaldehyde

Conditions

Workup

1. 1
   OtherThe solvent was removed under reduced pressure, and ethyl acetate
2. 2
   workup.ADDITIONan aqueous saturated sodium hydrogen carbonate solution were added
3. 3
   OtherThe organic layer was separated
4. 4
   Extractionthe aqueous layer was extracted with ethyl acetate
5. 5
   Washthe resultant solution was washed with an aqueous saturated sodium chloride solution
6. 6
   Dryingdried over anhydrous magnesium sulfate
7. 7
   Otherthe solvent was removed under reduced pressure

Procedure

To 0.42 g of 1-(1,3-dioxolan-2-ylmethyl)-6-isopropylquinolin-2(1H)-one, 4 mL of a 90% aqueous trifluoroacetic acid solution was added, and the mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure, and ethyl acetate and an aqueous saturated sodium hydrogen carbonate solution were added thereto. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain 0.41 g of a pale yellow oily substance, (6-isopropyl-2-oxoquinolin-1(2H)-yl)acetaldehyde.

Source