Propargyl alcohol → Prop-2-ynyl 3-oxopentanoate

HRID 1471328Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1471328
[O:1]=[C:2]([CH2:8][CH3:9])[CH2:3][C:4]([O:6][CH3:7])=[O:5].[CH2:10](O)[C:11]#C>C1(C)C=CC=CC=1.II>[O:1]=[C:2]([CH2:8][CH3:9])[CH2:3][C:4]([O:6][CH2:7][C:10]#[CH:11])=[O:5]

Komponenten

5

Edukt 2

HCID 7859Propargyl alcoholHCID 121699Methyl 3-oxovalerate

Produkt 1

HCID 58512883Prop-2-ynyl 3-oxopentanoateAusbeute 43,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 807IodineKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
115 °C

Versuchsvorschrift

To a solution of methyl 3-ketopentanoate (3) (822 mg, 6.00 mmol) and 2-propynol (686 mg, 12.0 mmol) in toluene (7 mL) is added I2 (46 mg, 0.18 mmol). The mixture is stirred at 115° C. for 6 h, then cooled to room temperature, and extracted with ethyl acetate (100 mL). The extract is washed (brine) and dried. After solvent removal at reduced pressure, the residue is distilled (125-130° C., 2 mm) to give 401 mg (43%) of 4 as a colorless liquid. IR 3345, 2856, 1715, 1456 cm−1; 1H NMR (CDCl3) δ 1.10 (t, J=7.5 Hz, 3H, CH2CH3), 2.52 (t, J=2.4 Hz, 1H, CH≡CCH2), 2.58 (q, J=7.5 Hz, 2H, CH2CH3) 3.51 (s, 2H, CH2), 4.74 (d, J=2.4 Hz, 2H, CH≡CCH2).

Aufarbeitung

  1. temperaturecooled to room temperature
  2. extractionextracted with ethyl acetate (100 mL)
  3. washThe extract is washed (brine)
  4. customdried
  5. customAfter solvent removal at reduced pressure
  6. distillationthe residue is distilled (125-130° C., 2 mm)

Quellen und Nachweise

ORD-Eintrag
ord-bcae3fa0d79f490eb7d2bc8b3b520f5b
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09012217B2

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