Water → 3-Ethyl-5-(2-methoxyethoxymethoxyphenyl)-2-cyclohexenone

HRID 1446982Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1446982
C(O[C:4]1[CH2:9][CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH3:22])[CH2:7][C:6](=[O:23])[CH:5]=1)C.[CH2:24]([Li])[CH3:25].O>C1C=CC=CC=1>[CH2:24]([C:4]1[CH2:9][CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH3:22])[CH2:7][C:6](=[O:23])[CH:5]=1)[CH3:25]

Komponenten

5

Edukt 3

HCID 962WaterHCID 205521113-Ethoxy-5-(2-methoxyethoxymethoxyphenyl)-2-cyclohexenoneHCID 178506846HCID 178506846, Verbindung

Produkt 1

HCID 205521173-Ethyl-5-(2-methoxyethoxymethoxyphenyl)-2-cyclohexenone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel2×

Versuchsvorschrift

A solution of 3-ethoxy-5-(2-methoxyethoxymethoxyphenyl)-2-cyclohexenone (2.0 g) in benzene (60 ml) was added dropwise with stirring in an atmosphere of dry nitrogen to an ice-cooled 1.5 M solution of ethyllithium in benzene (20.8 ml). When the addition was complete, water was added and the mixture was allowed to stand overnight at room temperature. The benzene layer was separated and the aqueous layer was extracted with ether. The organic solutions were combined, dried and the solvents were evaporated under reduced pressure. The residue was purified by preparative-layer chromatography on silica gel using a mixture of ethyl acetate and petroleum ether (b.p. 60°-80°) for elution to afford the title compound (0.65 g) as a pale yellow oil. (Found: C, 70.9; H, 7.7. C18H24O4 requires C, 71.0; H, 7.9%.)

Aufarbeitung

  1. additionWhen the addition
  2. customThe benzene layer was separated
  3. extractionthe aqueous layer was extracted with ether
  4. customdried
  5. customthe solvents were evaporated under reduced pressure
  6. customThe residue was purified by preparative-layer chromatography on silica gel using
  7. additiona mixture of ethyl acetate and petroleum ether (b.p. 60°-80°)
  8. washfor elution

Quellen und Nachweise

ORD-Eintrag
ord-c5fe46a367fe4ec0b1f2824a37ea6ece
Quelldatensatz
uspto-grants-1982_02
Patentnummer
US04315006

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