Reaktion #47966

Reaktionsgleichung

dimethyl sulfide

4-allyl-5,6-difluoro-4-(4-fluorophenyl)-3-(2,2,2-trifluoroethyl)-3,4-dihydroquinazolin-2(1H)-one

ozone

→

[5,6-Difluoro-4-(4-fluorophenyl)-2-oxo-3-(2,2,2-trifluoroethyl)-1,2,3,4-tetrahydroquinazolin-4-yl]acetaldehyde

Lösungsmittel

EtOAc

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe ozone was removed
2. 2
   Waschenwashed three times with water and brine
3. 3
   TrocknenThe organic layer was dried over NaSO4
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated in vacuo

Vorschrift

To a −78° C. solution of 2.6 g (6.495 mmol) 4-allyl-5,6-difluoro-4-(4-fluorophenyl)-3-(2,2,2-trifluoroethyl)-3,4-dihydroquinazolin-2(1H)-one in 25 ml MeOH was bubbled ozone. After 15 mins at −78° C., the ozone was removed and the reaction mixture was quenched with 4.8 mL (64.946 mmol) dimethyl sulfide. After stirring at room temperature overnight, the reaction mixture was diluted with EtOAc and washed three times with water and brine. The organic layer was dried over NaSO4, filtered and concentrated in vacuo. Afforded [5,6-difluoro-4-(4-fluorophenyl)-2-oxo-3-(2,2,2-trifluoroethyl)-1,2,3,4-tetrahydroquinazolin-4-yl]acetaldehyde. 1H NMR (CDCl3, 400 MHz) δ 9.79 (s, 1H, O═CH); 8.61 (br s, 1H, ArNHC═O); 7.38-7.27 (m, 2H, ArH); 7.15-7.03 (m, 3H, ArH); 6.57-6.53 (m, 1H, ArH); 4.08 (m, 1H, C); 3.72 (dd, 1H, J=17.4 Hz, CH2C═O); 3.50 (dd, 1H J=1.28 Hz, 17.58 Hz, CH2C═O); 3.32 (m, 1H, CH2C═O). ES MS+1=403.1.

Quelle