But-2-enal → HCID 54569326, compound

HRID 2309673Notes

Reaction equation

HRID 2309673 reaction equation
[CH3:1][C:2](=[CH:5][CH2:6][CH:7]1[CH2:11][CH:10]=[C:9]([CH3:12])[C:8]1([CH3:14])[CH3:13])[CH:3]=[O:4].C(=O)C=CC.CC(C)([O-])C.[K+]>COCCOC>[CH3:1][CH:2]([CH:5]=[CH:6][CH:7]1[CH2:11][CH:10]=[C:9]([CH3:12])[C:8]1([CH3:13])[CH3:14])[CH2:3][OH:4]

Participants

5

Reactant 3

HCID 20138But-2-enal2×HCID 30175572-Methyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)but-2-enalHCID 23665647Potassium tert-butoxide

Product 1

HCID 54569326HCID 54569326, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

The aldehyde, 2-methyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)but-2-enal, which had been prepared by using the procedure outlined in U.S. Pat. No. 4,052,341 Example IV-1, was reacted essentially following the procedure described in Example I for isomerizing the α,β double bond to the β,γ position. In this case the butenal (19.2 g, 0.1 mole) was reacted with potassium t-butoxide (16.8 g, 0.15 mole) in 1,2-dimethoxyethane (DME, 200 ml) at 15°-20° C. by feeding in the butenal over 30 minutes, stirring for an additional 15 minutes and then rapidly quenching with aqueous 20% acetic acid (75 ml).

Workup

  1. customrapidly quenching with aqueous 20% acetic acid (75 ml)

Sources & evidence

ORD record
ord-66363c39052146d189f5c59fbf0d863d
Source dataset
uspto-grants-1987_09
Patent number
US04696766

Reaction notes

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