Acrolein → 6,6-dimethylhept-1-en-4-yn-3-ol

HRID 413979Notes

Reaction equation

[C:1]([C:5]#[CH:6])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[CH:12]([CH:14]=[CH2:15])=[O:13]>>[CH3:2][C:1]([CH3:4])([CH3:3])[C:5]#[C:6][CH:12]([OH:13])[CH:14]=[CH2:15]

Participants

Reactant 3

HCID 7847Acrolein

HCID 135123,3-Dimethyl-1-butyne

HCID 178418339Butyllithium

Product 1

HCID 109755616,6-dimethylhept-1-en-4-yn-3-ol

Conditions

Temperature: -75 °C

Procedure

Reacting t-butylacetylene at −20° C. with butyllithium, cooling the reaction mixture to −75° C. and reacting it with acrolein to give 6,6-dimethylhept-1-en-4-yn-3-ol.

Workup

customat −20° C.

Sources & evidence

ORD record: ord-5567b88f6f28441c8585afa6254808db
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06570044B2

Reaction notes

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