Réaction #1859126

Équation de réaction

NaHCO3

7-hydroxy-4-(trifluoromethyl)-2H-chromen-2-one

tert-butyl (2-bromoethyl)carbamate

K2CO3

→

title compound

Rendement 87.0%

tert-Butyl (2-((2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl)oxy)ethyl)carbamate

Rendement 87.0%

Solvants

Ethyl acetate

DMF

Conditions de réaction

Traitement

1. 1
   AutreThe organic layer was separated
2. 2
   Extractionthe aqueous layer was extracted with Ethyl acetate
3. 3
   LavageThe combined organic extracts were washed with brine
4. 4
   Séchagedried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated
7. 7
   AutreThe crude product was purified by flash column chromatography

Mode opératoire

To a solution of 7-hydroxy-4-(trifluoromethyl)-2H-chromen-2-one (213 mg, 0.925 mmol) in DMF (1.5 mL) was added tert-butyl (2-bromoethyl)carbamate (416 mg, 1.851 mmol) and K2CO3 (384 mg, 2.776 mmol) at r.t. After stirred at 85° C. for 12 hours, the reaction mixture treated with 10.0 mL of saturated aqueous NaHCO3 solution. The organic layer was separated and the aqueous layer was extracted with Ethyl acetate. The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. The crude product was purified by flash column chromatography using a 9:1 v/v Hexane:Ethyl acetate as solvent to afford title compound (300 mg, 87% yield) as a white solid. 1H NMR 300 MHz (CDCl3) δ 7.64 (d, J=6.0 Hz, 1H), 6.91 (m, 2H), 6.61 (s, 1H), 4.95 (s, 1H), 4.11 (m, 2H), 3.58 (m, 2H), 1.56 (s, 9H), HRMS (m/z): [M+H]+ calculated for C17H18F3NO5. found, 374.1207.

Source