Formic Acid → 3-{[3-Fluoro-4-(methylsulfonyl)-phenyl]methylene}-2,4-pentanedione

HRID 1532273Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[S:10]([CH3:13])(=[O:12])=[O:11])[CH:5]=O.N1CCCCC1.C(O)=O.[CH3:23][C:24](=[O:29])[CH2:25][C:26](=[O:28])[CH3:27]>CN(C=O)C.O>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:25]([C:24](=[O:29])[CH3:23])[C:26](=[O:28])[CH3:27])[CH:7]=[CH:8][C:9]=1[S:10]([CH3:13])(=[O:12])=[O:11]

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution containing 0.93 g 3-fluoro-4-methylsulfonylbenzaldehyde, 0.05 ml piperidine and 0.02 ml formic acid in 20 ml DMF was added 1.04 ml 2,4-pentanedione with stirring at 20° C. The solution was stirred overnight at 20° C. and poured into water. The product was extracted with ethyl acetate and washed with water and evaporated to dryness in vacuo. The residue was crystallized from methanol, yield 0.48 g (30%), mp. 140-143° C. 1H-NMR (DMSO-d6, 400 MHz): 2.28 (s, 3 H, CH3), 2.50 (s, 3 H, CH3), 3.36 (s, 3 H, CH3), 7.47 (m, 1 H, Ar), 7.93 (m, 2 H, Ar), 7.76 (s, 1 H, CH).

Workup

stirringThe solution was stirred overnight at 20° C.
extractionThe product was extracted with ethyl acetate
washwashed with water
customevaporated to dryness in vacuo
customThe residue was crystallized from methanol, yield 0.48 g (30%), mp. 140-143° C

Sources & evidence

ORD record: ord-3440cfa0cadc48578545e8061e426742
Source dataset: uspto-grants-2001_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06201027B1

Reaction notes

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