Water → 2,2-Dimethylpropyl [2-(1-cyclohexenyl)-4-oxo-4H-[1]-benzopyran-8-yl)acetate

HRID 1200191Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1200191
[C:1]1([C:7]2[O:8][C:9]3[C:17]([CH2:18][C:19]([OH:21])=[O:20])=[CH:16][CH:15]=[CH:14][C:10]=3[C:11](=[O:13])[CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[CH3:34][C:35]([CH3:39])([CH3:38])[CH2:36]O.O>CN(C)C=O>[C:1]1([C:7]2[O:8][C:9]3[C:17]([CH2:18][C:19]([O:21][CH2:34][C:35]([CH3:39])([CH3:38])[CH3:36])=[O:20])=[CH:16][CH:15]=[CH:14][C:10]=3[C:11](=[O:13])[CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 6404Neopentyl alcoholHCID 682631,1'-CarbonyldiimidazoleHCID 14650449HCID 14650449, Verbindung

Produkt 1

HCID 146504632,2-Dimethylpropyl [2-(1-cyclohexenyl)-4-oxo-4H-[1]-benzopyran-8-yl)acetateAusbeute 23 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

[2-(1-Cyclohexenyl)-4-oxo-4H-[1]-benzopyran-8-yl]acetic acid (2.84 g) was dissolved in dimethylformamide (30 ml) and carbodiimidazole (1.78 g) was added to the solution. After stirring at room temperature for 2 hours, 2,2-dimethyl-propanol (0.88 g) was added. After stirring at 60° C. for 4 hours, water was added and the mixture was extracted with ethyl acetate. The extracted layer was washed with water, dried and concentrated. The residue was purified by silica gel column chromatography to obtain the title compound (0.82 g), yield 23%, m.p. 138°-139° C. (recrystallized from hexane-ethyl acetate).

Aufarbeitung

  1. stirringAfter stirring at 60° C. for 4 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extracted layer was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography
  7. customto obtain
  8. customthe title compound (0.82 g), yield 23%, m.p. 138°-139° C. (recrystallized from hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-c615cf7999374561b39b79dc8b30d5df
Quelldatensatz
uspto-grants-1990_02
Patentnummer
US04904690

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