1-Hexene → 8Z-Tridecenyl acetate

Reaction equation

[CH2:1]=[CH:2][CH2:3][CH2:4]CC.[C:7]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]=[CH2:19])(=[O:9])[CH3:8]>>[C:7]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]/[CH:18]=[CH:19]\[CH2:1][CH2:2][CH2:3][CH3:4])(=[O:9])[CH3:8]

Participants

Reactant 2

HCID 115971-Hexene

HCID 15673852Non-8-enyl acetate

Product 1

HCID 100145388Z-Tridecenyl acetate

Procedure

Reactions between 1-hexene and 8-nonenyl acetate were conducted using methods analogous to those described above using to form the pheromone derivative 17. When catalyzed by Ruthenium complex 1, the reaction proceeded in good yield (67%) with high Z-selectivity (91%) at a low catalyst loading (0.5 mol %).

Workup

customto form the pheromone derivative 17
customin good yield (67%) with high Z-selectivity (91%) at a low catalyst loading (0.5 mol %)

Sources & evidence

ORD record: ord-d311f3ee92db431b8a0eb371d8b2f2af
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987531B2

Reaction notes

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