Pyridine → HCID 86678083, compound

HRID 2274706Notes

Reaction equation

HRID 2274706 reaction equation
[C:1](Cl)(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17]C.C[C:22]1(C)[O:29][C:27](=[O:28])[CH2:26][C:24](=[O:25])O1.N1C=CC=CC=1>C(Cl)Cl>[O:25]=[C:24]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]/[CH:8]=[CH:9]\[CH2:10]/[CH:11]=[CH:12]\[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:26][C:27]([O:29][CH3:22])=[O:28]

Participants

5

Reactant 3

HCID 1049PyridineHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 9817754Linoleoyl chloride

Product 1

HCID 86678083HCID 86678083, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Linoleoyl chloride (25.0 g, 83.6 mmol) was added, dropwise, to a cooled (0° C.) solution of Meldrum's acid (1) (13.3 g, 92.0 mol) and pyridine (14.8 mL, 184 mmol) in CH2Cl2 (180 mL) and the solution was allowed to warm (rt, 16 h). The reaction mixture was washed with an equal volume of HCl (5%, aq., 2×), dried (Na2SO4), filtered and concentrated. The residue was dissolved in dry methanol (200 mL) and heated at reflux (6 h). The solution was cooled (rt), concentrated and the crude oil was purified by flash chromatography (4% EtOAc-hexanes) to yield (11Z,14Z)-methyl 3-oxoicosa-11,14-dienoate (2) (24.5 g, 87%) as a pale yellow oil. Rf 0.38 (10% EtOAc-hexanes). FW 336.51, C21H36O3.

Workup

  1. washThe reaction mixture was washed with an equal volume of HCl (5%, aq., 2×)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in dry methanol (200 mL)
  6. temperatureheated
  7. temperatureat reflux (6 h)
  8. temperatureThe solution was cooled (rt)
  9. concentrationconcentrated
  10. customthe crude oil was purified by flash chromatography (4% EtOAc-hexanes)

Sources & evidence

ORD record
ord-01e18c07cf424477a1fc263475c25e41
Source dataset
uspto-grants-2015_09
Patent number
US09126966B2

Reaction notes

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