Pyridine → (Z,E)-9,12-Tetradecadienyl acetate

HRID 879044Notes

Reaction equation

HRID 879044 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]\[CH2:24]/[CH:25]=C/C.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]/[CH:19]=[CH:18]\[CH2:17]/[CH:16]=[CH:15]/[CH3:14])(=[O:7])[CH3:6]

Participants

7

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 5365760(9z,12e)-Tetradecadien-1-ol

Product 1

HCID 5365642(Z,E)-9,12-Tetradecadienyl acetateYield 89.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (3.1 mmol, 0.29 mL), then pyridine (1.8 mmol, 0.14 mL), were added sequentially to alcohol 15 (1.5 mmol, 0.32 g) in CH2Cl2 (3 mL), and stirred at room temperature for 18 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, 10% EtOAc in hexanes) provided 16 (0.34 g, 89% yield, 88% Z as determined by 1H-NMR) as a colorless oil; 1H NMR (CDCl3): δ 5.31-5.49 (4H, m), 4.05 (2H, t, J=6.8 Hz), 2.72 (2H, m), 2.05 (3H, s), 2.02 (2H, m), 1.65 (2H, m), 1.61 (2H, m), 1.24-1.38 (11H, m); 13C NMR (CDCl3): δ 171.3, 130.4, 129.6, 127.7, 125.1, 64.7, 30.4, 29.6, 29.4, 29.2 (2C), 28.6, 27.1, 25.9, 21.0, 17.9; HRMS (FAB): 251.2000, [C16H28O2−H]+ requires 251.2011.

Workup

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

Sources & evidence

ORD record
ord-2c57b12ac2314846819bd22eba9ba342
Source dataset
uspto-grants-2015_03
Patent number
US08987531B2

Reaction notes

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