Benzaldehyde → 1-Phenyl-2-(4-methylthiophenyl)-1-buten-3-one

HRID 343081Notes

Reaction equation

HRID 343081 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](=[O:12])[CH3:11])=[CH:5][CH:4]=1.[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.N1CCCCC1>C1C=CC=CC=1>[C:14]1([CH:13]=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([S:2][CH3:1])=[CH:4][CH:5]=2)[C:10](=[O:12])[CH3:11])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 8082PiperidineHCID 134577081-[4-(Methylsulfanyl)phenyl]propan-2-one

Product 1

HCID 543926211-Phenyl-2-(4-methylthiophenyl)-1-buten-3-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 1-(4-methylthiophenyl)-2-propanone [G. Y. Lesher, U.S. Pat. No. 4,517,192, May 14, 1985; L. M. Werfel et al, J. Med. Chem., 29, 924-36 (1986)] (11.2 g, 0.062 mol) and benzaldehyde (6.6 g, 0.062 mol) in benzene (75 ml) containing piperidine (200 mg) was heated at reflux for 24 hours. After cooling, the solvent was removed and the residue was purified by chromatography on silica gel using mixtures of ethyl acetate and toluene to give the ketone. This material was recrystallized from ethyl acetate and hexane to give 14 g (82%) of pure ketone as a crystalline solid: mp 91°-93° C. Anal. Calc'd. for C17H16OS (268.38): C, 76.08; H, 6.01; S, 11.95. Found: C, 76.15; H, 6.08; S, 11.79.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 hours
  3. temperatureAfter cooling
  4. customthe solvent was removed
  5. customthe residue was purified by chromatography on silica gel using mixtures of ethyl acetate and toluene

Sources & evidence

ORD record
ord-84c9ac62d838489aa7f4f874b2961610
Source dataset
uspto-grants-1999_01
Patent number
US05859257

Reaction notes

Loading…