Dimethyl Sulfoxide → 2,5-Hexanedione
Reaction equation
CS(C)=O.[C:5](Cl)(=[O:9])[C:6](Cl)=O.CC1[N:13]([CH:18]([CH3:22])[CH:19]([OH:21])[CH3:20])C(C)=CC=1>C(Cl)Cl.C(O)(=O)C>[NH2:13][CH:18]([CH3:22])[CH:19]([OH:21])[CH3:20].[CH2:18]([CH2:22][C:5](=[O:9])[CH3:6])[C:19]([CH3:20])=[O:21]Participants
7
Reactant 3
Product 2
Reagents, catalysts & solvents 2
Procedure
To a solution of dimethylsulfoxide (1.56 g, 20.0 mmoles) and oxalyl chloride (1.9 g, 15.0 mmoles) in 20 ml of methylene chloride cooled to -78° C. was added 1.67 g (10.0 mmoles) of 3-(2,5-dimethylpyrrol-1-yl)-2-butanol obtained by dehydration cyclization of 3-amino-2-butanol and acetonylacetone in acetic acid. One hour later, 3 ml of triethylamine was added, and the mixture stirred at room temperature for 5 hours. The mixture was extracted with chloroform. The chloroform layer was dried over anhydrous magnesium sulfate, and concentrated, and chromatographed on a column of silica gel using cyclohexane/ethyl acetate (4/1) as an eluent to afford 3-(2,5-dimethylpyrrol-1-yl)-2-butanone (990 mg, 6.0 mmoles, 60%).
Sources & evidence
- ORD record
- ord-4dae3e76f8c44ba2b38390d9a9a6dd4d
- Source dataset
- uspto-grants-1980_11
- Patent number
- US04233309
Reaction notes
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