Isopropanol → 3-{[4-Chloro-3-(methylsulfonyl)phenyl]methylene}-2,4-pentanedione

HRID 1532287Notes

Reaction equation

[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[S:10]([CH3:13])(=[O:12])=[O:11].CC(O)C.[CH3:18][C:19](=[O:24])[CH2:20][C:21](=[O:23])[CH3:22].N1CCCCC1>C(O)=O>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[C:20]([C:19](=[O:24])[CH3:18])[C:21](=[O:23])[CH3:22])=[CH:4][C:3]=1[S:10]([CH3:13])(=[O:12])=[O:11]

Participants

Conditions

Temperature: 23.5 °C

Procedure

4-Chloro-3-(methylsulfonyl)benzaldehyde (760 mg), 2-propanol (10 mL), 2,4-pentanedione (0.8 mL), formic acid (22 mL) and piperidine (57 mL) were mixed and stirred at 22-25° C. for 20 h. The product was filtered, washed with 2-propanol and dried. The compound was purified by crystallization from toluene (15 mL, yield 790 mg, melting point 170-172° C.). 1H-NMR (400 MHz, DMSO-d6) d=2.27 (s, 3H), 2.47 (s, 3H), 3.40 (s, 3H), 7.72 (dd, J=8.3 Hz, 2.2 Hz, 1H), 7.84 (d, J=8.3 Hz, 1H), 7.84 (s, 1H), 8.19 (d, J=2.2 Hz, 1H).

Workup

filtrationThe product was filtered
washwashed with 2-propanol
customdried
customThe compound was purified by crystallization from toluene (15 mL, yield 790 mg, melting point 170-172° C.)

Sources & evidence

ORD record: ord-7692dae463a74359b2338738cf3b849b
Source dataset: uspto-grants-2001_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06201027B1

Reaction notes

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