Potassium Carbonate → ethyl 6-nitro-2-(trifluoromethyl)-2H-1-benzopyran-3-carboxylate

HRID 722292

Reaktionsgleichung

Reaktionsgleichung von HRID 722292
[N+:1]([C:4]1[CH:11]=[C:8]([CH:9]=O)[C:7]([OH:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[F:13][C:14]([F:23])([F:22])/[CH:15]=[CH:16]/[C:17]([O:19][CH2:20][CH3:21])=[O:18].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O.C(OCC)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH:15]([C:14]([F:13])([F:23])[F:22])[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:9][C:8]=2[CH:11]=1)([O-:3])=[O:2]

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 668085-NitrosalicylaldehydeHCID 5371261Ethyl (2E)-4,4,4-trifluoro-2-butenoate

Produkt 1

HCID 21883718ethyl 6-nitro-2-(trifluoromethyl)-2H-1-benzopyran-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 5-nitrosalicylaldehyde (4.80 g, 28.7 mmol) and ethyl 4,4,4-trifluorocrotonate (6.6 g, 39.4 mol) in anhydrous DMF was warmed to 60° C. and treated with anhydrous K2CO3 (3.90 g, 28.9 mol). The solution was maintained at 60° C. for 20 hours, cooled to room temperature, diluted with water, and extracted with ethyl acetate. The organic extracts were washed with brine, dried over anhydrous MgSO4, filtered and concentrated in vacua to afford an oil. The oil was dissolved in diethyl ether (5 mL). Hexanes was added until the solution became cloudy. Upon standing at room temperature overnight the ester was obtained as yellow crystals (0.856 g, 7% yield). This material was of sufficient purity to be used in subsequent steps without further purification. 1H NMR (CDCl3/300 MHz) 8.15–8.19 (m, 2H), 7.74 (s, 1H), 7.09 (d, 1H, J=8.9 Hz), 5.81 (q, 1H, J=5.8 Hz), 4.29–4.39 (m, 2H), 1.35 (t, 3H, J=6.0 Hz),

Aufarbeitung

  1. temperatureThe solution was maintained at 60° C. for 20 hours
  2. temperaturecooled to room temperature
  3. extractionextracted with ethyl acetate
  4. washThe organic extracts were washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacua
  8. customto afford an oil

Quellen und Nachweise

ORD-Eintrag
ord-684e61751e574bbc8516c34e94ddaa94
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07138411B2

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