Dimethyl Sulfoxide → 11-Hexadecenal, (11Z)-

HRID 879035

Reaktionsgleichung

Reaktionsgleichung von HRID 879035
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH2:11]([OH:27])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23][CH2:24][CH2:25][CH3:26].C(N(CC)CC)C>C(Cl)Cl.CCOCC>[CH:11](=[O:27])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23][CH2:24][CH2:25][CH3:26]

Komponenten

7

Edukt 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 5283305Virelure

Produkt 1

HCID 536449511-Hexadecenal, (11Z)-Ausbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

DMSO (0.11 mL, 1.6 mmol) was added dropwise to a solution of oxalyl chloride (0.080 mL, 0.96 mmol) in CH2Cl2 (5 mL) at −78° C., and after 5 minutes a solution of alcohol 5 (0.21 g, 0.87 mmol) in CH2Cl2 (0.9 mL) was added. After stirring for 15 minutes at the same temperature, triethylamine (0.61 mL, 4.4 mmol) was added. The mixture was warmed to room temperature, diluted with Et2O, washed sequentially with 1M HCl, saturated aqueous NaHCO3, brine, dried with Na2SO4, and the solvent was removed in vacuo. Flash chromatography of the residue (SiO2, 10% EtOAc in hexanes) provided 6 (0.20 g, 95% yield, 86% Z as determined by 1H-NMR) as a colorless oil; 1H NMR (CDCl3): δ 9.76 (1H, t, J=1.9 Hz), 5.36 (2H, m), 2.42 (2H, td, J=7.4, 1.9 Hz), 2.02 (4H, m), 1.63 (2H, m), 1.24-1.36 (16H, m), 0.90 (3H, t, J=7.2 Hz); 13C NMR (CDCl3): δ 202.9, 129.9, 129.8, 43.9, 32.0, 29.8, 29.5, 29.4 (2C), 29.3, 29.2, 27.2, 26.9, 22.4, 22.1, 14.0; HRMS (FAB): 237.2209, [C16H30O−H]+ requires 237.2218.

Aufarbeitung

  1. additionwas added
  2. washwashed sequentially with 1M HCl, saturated aqueous NaHCO3, brine
  3. dry with materialdried with Na2SO4
  4. customthe solvent was removed in vacuo
  5. customFlash chromatography of the residue (SiO2, 10% EtOAc in hexanes) provided 6 (0.20 g, 95% yield, 86% Z as determined by 1H-NMR) as a colorless oil

Quellen und Nachweise

ORD-Eintrag
ord-8a33d951905d466c8104057395d84a13
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987531B2

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