Hydrochloric Acid → Ethylcyclohexyl(oxo)acetate

HRID 471803

Reaktionsgleichung

Reaktionsgleichung von HRID 471803
[Mg].[CH:2]1(Br)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH2:9]([O:11][C:12](=[O:18])[C:13](OCC)=[O:14])[CH3:10].Cl>C1COCC1>[CH:2]1([C:13](=[O:14])[C:12]([O:11][CH2:9][CH3:10])=[O:18])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 7960Cyclohexyl bromideHCID 5462224Magnesium

Produkt 1

HCID 11041407Ethylcyclohexyl(oxo)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a suspension of magnesium turnings (2.20 g, 90.32 mmol) in THF (100 mL) was added cyclohexyl bromide (9.27 mL, 75.27 mmol). The mixture was sonicated (note 1) for 30 min, the supernatant liquid was decanted into an addition funnel and added to a solution of diethyloxalate (22.0 g, 146.14 mmol) in THF (240 mL) at −10° C. over one hour. After 30 minutes, 10% HCl (75 mL) was added the mixture was and stirred 15 minutes. Layers were separated and the aqueous layer was extracted with Et2O (100 mL). Combined organics were washed (brine), dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording the title compound as a clear oil. 1H NMR (400 MHz, CDCl3) δ ppm 1.15-1.40 (m, 5H) 1.56-1.94 (m, 8H) 2.97-3.05 (m, 1H) 4.30 (q, J=7.32 Hz, 2H).

Aufarbeitung

  1. customThe mixture was sonicated (note 1) for 30 min
  2. customthe supernatant liquid was decanted into an addition funnel
  3. customLayers were separated
  4. extractionthe aqueous layer was extracted with Et2O (100 mL)
  5. washCombined organics were washed (brine)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography (EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-ecec9907c0f64ee8bb47f10ab05bec18
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633175B2

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