Acetone → 1,5-Bis(4-fluorophenyl)-1,4-pentadien-3-one

HRID 565127Notes

Reaction equation

[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH3:10][C:11]([CH3:13])=[O:12]>>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH:10][C:11](=[O:12])[CH:13]=[CH:6][C:5]2[CH:8]=[CH:9][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 180Acetone

HCID 680234-Fluorobenzaldehyde

Product 1

HCID 12682491,5-Bis(4-fluorophenyl)-1,4-pentadien-3-one

Procedure

Commercially available 4-fluorobenzaldehyde of formula V-1 is condensed with acetone, under basic conditions, to provide 1,5-Bis-(4-fluorophenyl)-penta-1,4-dien-3-one of formula V-2. The dienone is reduced with magnesium in methanol to provide the ketone of formula V-3. The ketone of formula V-3 is converted to dihydropyrone products of formula V-8 using chemistry analogous to that described in Chart U for the sequence of reactions from U-3 to U-8.

Sources & evidence

ORD record: ord-9717d8f3a89344649641bbc8764740a0
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06169181A

Reaction notes

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