Gamma-Valerolactone → Pentanamide, N-heptyl-5-hydroxy-

HRID 486081

Reaktionsgleichung

Reaktionsgleichung von HRID 486081
[C:1]1(=[O:7])O[CH:4]([CH3:5])[CH2:3][CH2:2]1.[CH2:8]([NH2:15])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].CCCCCC.C(OCC)(=[O:24])C>C1(C)C=CC=CC=1>[CH2:8]([NH:15][C:5](=[O:24])[CH2:4][CH2:3][CH2:2][CH2:1][OH:7])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Komponenten

6

Edukt 4

HCID 7921Gamma-ValerolactoneHCID 8058HexaneHCID 81271-HeptanamineHCID 8857Ethyl Acetate

Produkt 1

HCID 10262728Pentanamide, N-heptyl-5-hydroxy-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Part A. A solution of γ-valerolactone (25.0 g, 0.249 mol) in toluene (50 mL) and n-heptylamine (35.96 g, 0.312 mol) was heated to reflux for 18 hours under a nitrogen atmosphere. The reaction mixture was allowed to cool to ambient temperature, diluted with ethyl acetate (300 mL) and washed with 1 N aqueous HCl (50 mL), water and brine. The organic layer was dried over magnesium sulfate and then concentrated to give a white solid. The product was crystallized from ethyl ether:hexane to give N-heptyl-5-hydroxypentanamide (41.8 g, 0.194 mol) as white plates, mp 55°-56°. 1H NMR (CDCl3) δ6.06 (bs,1H), 3.61 (t,2H,J=7.3 Hz), 3.24 (quartet,2H,J=8.4 Hz), 3.19 (bs,1H), 2.19 (t,2H,J=8.3 Hz), 1.80-1.23 (m,14H), 0.86 (t,3H,J=6.0 Hz).

Aufarbeitung

  1. temperatureto reflux for 18 hours under a nitrogen atmosphere
  2. washwashed with 1 N aqueous HCl (50 mL), water and brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated
  5. customto give a white solid
  6. customThe product was crystallized from ethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-02155e9c27774d01b7ec6c37beff73e2
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05290801

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