Dimethylformamide → ethyl 8-iodo-7-methoxy-2-(trifluoromethyl)-2H-chromene-3-carboxylate

HRID 855023Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 855023
[OH:1][C:2]1[C:9]([I:10])=[C:8]([O:11][CH3:12])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[F:13][C:14](/[C:17](=C\C)/C(OCC)=O)([F:16])[F:15].C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)C=O.[C:36]([O:39][CH2:40][CH3:41])(=[O:38])[CH3:37]>>[I:10][C:9]1[C:8]([O:11][CH3:12])=[CH:7][CH:6]=[C:3]2[C:2]=1[O:1][CH:17]([C:14]([F:16])([F:15])[F:13])[C:37]([C:36]([O:39][CH2:40][CH3:41])=[O:38])=[CH:4]2

Komponenten

6

Edukt 5

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 190890572-Hydroxy-3-iodo-4-methoxybenzaldehydeHCID 23051828Ethyl trifluoromethylcrotonate

Produkt 1

HCID 58934894ethyl 8-iodo-7-methoxy-2-(trifluoromethyl)-2H-chromene-3-carboxylateAusbeute 14 %

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To the mixture of 1.5 g (5.4 mmol) of 2-hydroxy-3-iodo-4-methoxybenzaldehyde, 3.1 mL (20.6 mmol) of ethyl trifluoromethylcrotonate, and 4.2 g(12.9 mmol) of cesium carbonate was added 8 mL of anhydrous N,N-dimethylformamide. The mixture was heated to 90° C. overnight. After cooling to room temperature, to the reaction was added 150 mL of ethyl acetate. The organic solution was filtered, washed with brine and dried over anhydrous magnesium sulfate. After removing the volatiles, the residue was purified by silica chromatography with ethyl acetate/hexane (2:8) to give 0.3 g (14%) a light yellow solid: 1H NMR(CDCl3/400 MHz) 7.65(s, 1H), 7.17(d, J=8.4 Hz, 1H), 6.50(d, J=8.4 Hz, 1H), 5.80(q, J=6.8 Hz,1H), 4.30(m, 2H), 3.92(s, 3H), 1.33(t, J=7.6 Hz, 3H). MS (ESI+) 429.0(M+1, 100). HRMS (EI+) m/z calcd for (C14H12F3O4) 427.9732, found 427.9715.

Aufarbeitung

  1. temperatureAfter cooling to room temperature, to the reaction
  2. filtrationThe organic solution was filtered
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter removing the volatiles
  6. customthe residue was purified by silica chromatography with ethyl acetate/hexane (2:8)

Quellen und Nachweise

ORD-Eintrag
ord-85b4db35c8b64128bac6b94fbe2ef3c4
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07259266B2

Notizen zur Reaktion

Wird geladen…