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

HRID 1771944

Reaktionsgleichung

Reaktionsgleichung von HRID 1771944
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:13]([F:16])([F:15])[F:14])=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1.Br[CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24].C([O-])([O-])=O.[K+].[K+].C([O-])(O)=O.[Na+]>CN(C=O)C.C(OCC)(=O)C>[O:12]=[C:8]1[CH:7]=[C:6]([C:13]([F:16])([F:14])[F:15])[C:5]2[C:10](=[CH:11][C:2]([O:1][CH2:18][CH2:19][NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:3][CH:4]=2)[O:9]1

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 53756677-Hydroxy-4-trifluoromethylcoumarin

Produkt 1

HCID 86699721tert-Butyl (2-((2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl)oxy)ethyl)carbamateAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

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.

Aufarbeitung

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with Ethyl acetate
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-461862c62f3b4aeeb3539bc59581e950
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09249128B2

Verknüpfte Notizen

Wird geladen…