Hydrochloric Acid → 3-Ethynylcyclohex-2-en-1-one

HRID 1660644

Reaktionsgleichung

Reaktionsgleichung von HRID 1660644
[C:1]([Mg]Br)#[CH:2].C(O[C:8]1[CH2:13][CH2:12][CH2:11][C:10](=[O:14])[CH:9]=1)C.Cl>O1CCCC1>[C:1]([C:8]1[CH2:13][CH2:12][CH2:11][C:10](=[O:14])[CH:9]=1)#[CH:2]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 792163-Ethoxycyclohex-2-ene-1-oneHCID 178418486HCID 178418486, Verbindung

Produkt 1

HCID 145707953-Ethynylcyclohex-2-en-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 0.5N ethynylmagnesium bromide in tetrahydrofuran (100 mL) was added under N2 and stirring 3-ethoxy-2-cyclohexen-1-one (3.75 g, 26.8 mmol) in tetrahydrofuran (12.5 mL). The mixture was stirred at RT for 20 h when it was acidified with 1N HCl (200 mL). After stirring for 15 min the acidic phase was extracted with dichloromethane (5×50 mL). The combined organic extracts were washed with water (2×50 mL) and dried (MgSO4). Evaporation of the solvent gave an oil that was purified by column chromatography (silica, ethyl acetate/hexane 1:9) to yield a yellow oil, 2.71 g, 22.6 mmol, 84%). Analysis were in agreement with literature data.

Aufarbeitung

  1. stirringAfter stirring for 15 min the acidic phase
  2. extractionwas extracted with dichloromethane (5×50 mL)
  3. washThe combined organic extracts were washed with water (2×50 mL)
  4. dry with materialdried (MgSO4)
  5. customEvaporation of the solvent
  6. customgave an oil that
  7. customwas purified by column chromatography (silica, ethyl acetate/hexane 1:9)
  8. customto yield a yellow oil, 2.71 g, 22.6 mmol, 84%)

Quellen und Nachweise

ORD-Eintrag
ord-3b38e57ba70f4005a4ef34acb0ac9b79
Quelldatensatz
uspto-grants-2011_10
Patentnummer
USRE042802E1

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