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Water → (3E)-4-(5-acetoxy-3-methyl-1,3-pentadien-1-ylidene)3,5,5-trimethyl-2-cyclohexen-1-one

HRID 440220
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 440220
[OH:1][CH2:2]/[CH:3]=[C:4](\[CH3:17])/[CH:5]=[C:6]=[C:7]1[C:12]([CH3:14])([CH3:13])[CH2:11][C:10](=[O:15])[CH:9]=[C:8]1[CH3:16].C(N([CH2:23][CH3:24])CC)C.CNC1(NC)C=CN=CC1.[OH2:35]>CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O>[C:23]([O:1][CH2:2]/[CH:3]=[C:4](\[CH3:17])/[CH:5]=[C:6]=[C:7]1[C:12]([CH3:13])([CH3:14])[CH2:11][C:10](=[O:15])[CH:9]=[C:8]1[CH3:16])(=[O:35])[CH3:24]
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Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 22406474(3E)-4-(5-hydroxy-3-methyl-1,3-pentadien-1-ylidene)-3,5,5-trimethyl-2-cyclohexen-1-oneHCID 865890494,4-Dimethylaminopyridine

Produkt 1

HCID 22406473(3E)-4-(5-acetoxy-3-methyl-1,3-pentadien-1-ylidene)3,5,5-trimethyl-2-cyclohexen-1-oneAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterLösungsmittel

Versuchsvorschrift

To a solution of (3E)-4-(5-hydroxy-3-methyl-1,3-pentadien-1-ylidene)-3,5,5-trimethyl-2-cyclohexen-1-one (1.2 g, 5.2 mmol) in acetic anydride (5.0 mL) and triethylamine (5.0 mL) cooled to 0° C., was added 4,4-dimethylaminopyridine (25 ng). After 15 min. water was added to the reaction mixture, and the product was extracted three times with ether. The combined ethereal extracts were washed with sodium chloride solution, and dried over anhydrous sodium sulfate. Evaporation of the solvent and chromatography over silica gel in the manner described in Example 1 above gave the desired product (680 mg, 48%).

Aufarbeitung

  1. extractionthe product was extracted three times with ether
  2. washThe combined ethereal extracts were washed with sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customEvaporation of the solvent and chromatography over silica gel in the manner

Quellen und Nachweise

ORD-Eintrag
ord-62651b3f8d364f57a1810c34580df975
Quelldatensatz
uspto-grants-1996_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05518995

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