3-Butyn-2-ol → Undec-8-en-3-yne-2,5-diol

HRID 61344

Reaction equation

HRID 61344 reaction equation
[CH3:1][CH:2]([OH:5])[C:3]#[CH:4].C([Mg]Br)C.[CH:10](=[O:17])[CH2:11][CH2:12][CH:13]=[CH:14][CH2:15][CH3:16]>O1CCCC1>[CH3:1][CH:2]([OH:5])[C:3]#[C:4][CH:10]([OH:17])[CH2:11][CH2:12][CH:13]=[CH:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 162393-Butyn-2-olHCID 71590Hept-4-enalHCID 178418443HCID 178418443, compound

Product 1

HCID 123300045Undec-8-en-3-yne-2,5-diol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

But-3-yn-2-ol was added into a solution of ethyl magnesium bromide (EtMgBr) in tetrahydrofuran (THF). Hept-4-enal was then dropped into the mixture at room temperature and aged for 2 hours. The rush over process provided the product undec-8-en-3-yne-2,5-diol.

Sources & evidence

ORD record
ord-031d4fef6cf0407a9a44ce165221682a
Source dataset
uspto-grants-2016_09
Patent number
US09441185B2

Linked notes

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