Pyridine → 9-Dodecenyl acetate, (9Z)-

HRID 879037Notes

Reaction equation

HRID 879037 reaction equation
[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]\CC>C(Cl)Cl.C(OCC)C>[C:5]([O:4][CH2:1][CH2:2][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]/[CH:17]=[CH:16]\[CH2:15][CH3:14])(=[O:7])[CH3:6]

Participants

6

Reactant 3

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

Product 1

HCID 53634059-Dodecenyl acetate, (9Z)-Yield 87%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (0.17 mL, 1.8 mmol), then pyridine (90 μL, 1.1 mmol), were added sequentially to alcohol 7 (0.17 g, 0.93 mmol) in CH2Cl2 (1.8 mL), and stirred at room temperature for 17 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 8 (0.18 g, 87% yield, 74% Z as determined by 13C-NMR) as a colorless oil; 1H NMR (CDCl3): δ 5.28-5.43 (2H, m), 4.05 (2H, t, J=6.8 Hz), 2.04 (7H, m), 1.61 (2H, td, J=9.8, 8.7, 4.6 Hz), 1.29 (10H, m), 0.95 (3H, m); 13C NMR (CDCl3): δ 171.3, 131.6, 129.3, 64.7, 32.6, 29.8, 29.5, 29.3, 29.2, 28.7, 26.0, 21.1, 20.6, 14.5; HRMS (FAB): 227.2045, [C14H26O2+H]+ requires 227.2006.

Workup

  1. washwashed with saturated aqueous NaHCO3
  2. dry with materialbrine, dried with Na2SO4
  3. concentrationconcentrated
  4. customFlash chromatography of the residue (SiO2, 5% EtOAc in hexanes) provided 8 (0.18 g, 87% yield, 74% Z as determined by 13C-NMR) as a colorless oil

Sources & evidence

ORD record
ord-b686bf678fb84fc7ae1ce9cfe59676f2
Source dataset
uspto-grants-2015_03
Patent number
US08987531B2

Reaction notes

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