HCID 86657617, compound → HCID 86657616, compound

HRID 1770676Notes

Reaction equation

HRID 1770676 reaction equation
[C:1]([O:18][CH3:19])(=[O:17])[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][CH:15]=[CH2:16].C(OC)(=O)CCCCCCCC#CCC#CCC=C>C(OCC)(=O)C.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[C:1]([O:18][CH3:19])(=[O:17])[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][CH:15]=[CH2:16]

Participants

5

Reactant 2

HCID 86657617HCID 86657617, compoundHCID 86657618HCID 86657618, compound

Product 1

HCID 86657616HCID 86657616, compound

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

For the preparation of methyl hexadeca-9,12,15-trienoate, a solution of methyl hexadeca-15-en-9,12-diynoate (800 mg) in ethyl acetate (15 mL) was hydrogenated in the presence of Lindlar catalyst (300 mg) at ambient pressure using a balloon for 20 h. The catalyst was then removed by filtration, and the solvent was evaporated to yield (9Z,12Z)-methyl hexadeca-9,12,15-trienoate as the major product. A portion of the product was then purified by preparative thin layer chromatography using hexanes:ethyl acetate 98:2 (3 developments) to yield pure (9Z,12Z)-methyl hexadeca-9,12,15-trienoate. The characterization data for (9Z,12Z)-methyl hexadeca-9,12,15-trienoate is provided below.

Workup

  1. customfor 20 h
  2. customThe catalyst was then removed by filtration
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-95b86ff8fadc4f21b0592f6307636657
Source dataset
uspto-grants-2016_02
Patent number
US09248145B2

Reaction notes

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