4'-Fluoroacetophenone → 1-(4-Fluorophenyl)pentane-1,3-dione

HRID 2300609Notes

Reaction equation

[C:1]1([C:7](=[O:13])[CH2:8][C:9](=[O:12])[CH2:10][CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:14]C1C=CC(C(=O)C)=CC=1.C(OC)(=O)CC>>[F:14][C:4]1[CH:5]=[CH:6][C:1]([C:7](=[O:13])[CH2:8][C:9](=[O:12])[CH2:10][CH3:11])=[CH:2][CH:3]=1

Participants

Reactant 3

HCID 98284'-Fluoroacetophenone

HCID 11124Methyl propionate

HCID 21408Propionyl Acetophenone

Product 1

HCID 125477611-(4-Fluorophenyl)pentane-1,3-dione

Procedure

The title compound was prepared (as described above for Intermediate 16) from 0.525 g of 4′-fluoroacetophenone and 0.73 mL of methyl propionate to yield 120 mg of Intermediate 32: TLC analysis: Rf=0.77 (2/1, hexanes/EtOAc); 1H NMR (400 MHz, CDCl3, enol form) δ7.98 (d, 2H, J=8.3), 7.7 (d, 2H, J=8.3), 6.12 (s, 1H), 1.55 (s, 3H); low resolution mass spectrum (ES+) 195 (MH+)

Sources & evidence

ORD record: ord-e8edd345cf4b4b5fbe4e0385757e2407
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06498174B1

Reaction notes

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