Pyridine → 11-Tetradecenyl acetate, (11Z)-

HRID 879039

Reaktionsgleichung

Reaktionsgleichung von HRID 879039
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].N1C=CC=CC=1.[CH2:14](O)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]/[CH:22]=[CH:23]\[CH2:24][CH3:25].CCOC(C)=O>C(Cl)Cl.C(OCC)C>[C:5]([O:4][CH2:1][CH2:2][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]/[CH:17]=[CH:16]\[CH2:15][CH3:14])(=[O:7])[CH3:6]

Komponenten

7

Edukt 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 64313429-Dodecen-1-ol, (9Z)-

Produkt 1

HCID 536769211-Tetradecenyl acetate, (11Z)-Ausbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Acetic anhydride (0.17 mL, 1.8 mmol), then pyridine (86 μL, 1.1 mmol), were added sequentially to alcohol 7 (0.19 g, 0.89 mmol) in CH2Cl2 (1.8 mL), and stirred at room temperature for 12 hours. The mixture was diluted with diethyl ether, washed with saturated aqueous NaHCO3, then brine, dried with Na2SO4, and concentrated. Flash chromatography of the residue (SiO2, 5% EtOAc in hexanes) provided 10 (0.19 g, 84% yield, 77% Z as determined by 13C-NMR) as a colorless oil; 1H NMR (CDCl3): δ 5.29-5.43 (2H, m), 4.05 (2H, t, J=6.8 Hz), 2.04 (7H, m), 1.61 (2H, m), 1.27 (14H, m), 0.95 (3H, m); 13C NMR (CDCl3): δ 171.4, 131.7, 129.4, 64.8, 32.7, 29.9, 29.7 (2C), 29.4 (2C), 28.7, 27.2, 26.1, 21.2, 20.7, 14.6; HRMS (FAB): 255.2324, [C16H30O2+H]+ requires 255.2319.

Aufarbeitung

  1. washwashed with saturated aqueous NaHCO3
  2. dry with materialbrine, dried with Na2SO4
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-9fe16c1ab2ad4d1094adb4f38fd21263
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987531B2

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