Ethyl chloroacetate → HCID 86729430, Verbindung

HRID 629519Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 629519
[C:1]12([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([CH3:18])[CH:12]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]>CN(C)C=O.C(OCC)(=O)C>[C:1]12([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:13]([CH3:18])[CH:12]=3)[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2

Komponenten

6

Edukt 3

HCID 7751Ethyl chloroacetateHCID 11430Potassium CarbonateHCID 27950214-(1-adamantyl)-2-methylphenol

Produkt 1

HCID 86729430HCID 86729430, VerbindungAusbeute 95,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 4-(adamantan-1-yl)-2-methylphenol (2.0 g, 8.76 mmol) in N,N-dimethylformamide (10 mL) was added potassium carbonate (3.63 g, 23.29 mmol) and ethyl chloroacetate (1.29 g, 10.51 mmol), and stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate and washed with aqueous sodium bicarbonate. The organic layer was dried over anhydrous magnesium sulfate. The solvent was filtered and evaporated under reduced pressure to afford a crude solid, which was purified by silica gel column chromatography to give ethyl 2-(4-(adamantan-1-yl)-2-methylphenoxy)acetate as a white solid (2.6 g, 95.9% yield).

Aufarbeitung

  1. washwashed with aqueous sodium bicarbonate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationThe solvent was filtered
  4. customevaporated under reduced pressure
  5. customto afford a crude solid, which
  6. customwas purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3a2eac7df19649cdbb8266b40ac564e5
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09315507B2

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