Borane → 3,5-Pentadecadiene, 15-chloro-, (3Z,5Z)-

HRID 435216Notes

Reaction equation

HRID 435216 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]#[C:12]/[CH:13]=[CH:14]\[CH2:15][CH3:16].C1(BC2CCCCC2)CCCCC1.B>C(O)(=O)C>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]/[CH:11]=[CH:12]\[CH:13]=[CH:14]/[CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 6331BoraneHCID 13194925HCID 13194925, compoundHCID 15879360CID 15879360

Product 1

HCID 64380113,5-Pentadecadiene, 15-chloro-, (3Z,5Z)-

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

reducing the 15-chloro-(Z)-3-pentadecen-5-yne with dicyclohexyl borane followed by protonolysis of the product borane with acetic acid to obtain 15-chloro-(Z,Z)-3,5-pentadecadiene;

Sources & evidence

ORD record
ord-195e4a4b42b14c299377f9a48fe8c5b9
Source dataset
uspto-grants-1983_08
Patent number
US04400550

Reaction notes

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