Formic Acid → 3,3,4,4,4-pentafluorobutan-2-yl 4-((4-hydroxy-2-oxo-2H-chromen-3-yl)methyl)benzoate

HRID 2080703

Reaktionsgleichung

Reaktionsgleichung von HRID 2080703
C(O)=O.[OH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[O:8][C:7](=[O:15])[CH:6]=1.[CH:16]([C:18]1[CH:35]=[CH:34][C:21]([C:22]([O:24][CH:25]([C:27]([F:33])([F:32])[C:28]([F:31])([F:30])[F:29])[CH3:26])=[O:23])=[CH:20][CH:19]=1)=O.C(N(CC)CC)C>C(OCC)(=O)C>[OH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[O:8][C:7](=[O:15])[C:6]=1[CH2:16][C:18]1[CH:19]=[CH:20][C:21]([C:22]([O:24][CH:25]([C:27]([F:32])([F:33])[C:28]([F:30])([F:31])[F:29])[CH3:26])=[O:23])=[CH:34][CH:35]=1

Komponenten

6

Edukt 4

HCID 284Formic AcidHCID 8471TriethylamineHCID 546829304-HydroxycoumarinHCID 58930722HCID 58930722, Verbindung

Produkt 1

HCID 587609933,3,4,4,4-pentafluorobutan-2-yl 4-((4-hydroxy-2-oxo-2H-chromen-3-yl)methyl)benzoateAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

Formic acid (35.8 ml) was added to 4-Hydroxycoumarin (15.8 g, 97.5 mmol) and aldehyde 3 (28.9 g, 97.6 mmol). Triethylamine (43 ml) was added (exothermic) at 0° C. It was warmed to 140° C. and stirred for 4 h at this temperature. The yellow solution was cooled to rt, ethyl acetate was added, it was washed with 1 N HCl and brine, it was dried over Na2SO4 and the solvent was removed. The slightly yellow solid was recrystallized from ethylacetate to yield the title compound as a white solid in 98% purity (60% yield).

Aufarbeitung

  1. temperatureThe yellow solution was cooled to rt
  2. washit was washed with 1 N HCl and brine, it
  3. dry with materialwas dried over Na2SO4
  4. customthe solvent was removed
  5. customThe slightly yellow solid was recrystallized from ethylacetate

Quellen und Nachweise

ORD-Eintrag
ord-398119d19f004e6b82f821c94e905d35
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07932405B2

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