Ethyl Acetate → 1-(4-Hydroxycyclohexyl)propan-1-one

HRID 626109Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 626109
[CH3:1][CH2:2][Mg+].[Br-].[OH:5][CH:6]1[CH2:11][CH2:10][CH:9]([C:12](N(OC)C)=[O:13])[CH2:8][CH2:7]1.CCOC(C)=O>C1COCC1>[OH:5][CH:6]1[CH2:11][CH2:10][CH:9]([C:12](=[O:13])[CH2:2][CH3:1])[CH2:8][CH2:7]1

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 86642922HCID 86642922, VerbindungHCID 178461630HCID 178461630, Verbindung

Produkt 1

HCID 510398611-(4-Hydroxycyclohexyl)propan-1-oneAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

EtMgBr (1 M, 3.0 eq, 20 mL) was added to a solution of 4-hydroxy-N-methoxy-N-methylcyclohexanecarboxamide (1.0 g, 1.0 eq) in dry THF at 0° C. Once addition was complete, the mixture was stirred overnight. The reaction mixture was washed with saturated NH4Cl (aq), and extracted by EtOAc. The extract was dried, concentrated, and purified by column chromatography with petroleum ether:EtOAc=1:1 to give the desired product (0.6 g, 72% yield). 1H NMR (400 MHz, CDCl3) δ 3.50-3.64 (m, 1H), 2.47 (q, J=7.2 Hz, 2H), 2.28-2.37 (m, 1H), 2.00-2.10 (m, 2H), 1.88-1.94 (m, 2H), 1.70-1.80 (m, 1H), 1.21-1.49 (m, 4H), 1.05 (t, J=7.2 Hz, 3H).

Aufarbeitung

  1. additionOnce addition
  2. washThe reaction mixture was washed with saturated NH4Cl (aq)
  3. extractionextracted by EtOAc
  4. customThe extract was dried
  5. concentrationconcentrated
  6. custompurified by column chromatography with petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-9f37ee00452a44258c65951390588349
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309211B2

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