Dimethylformamide → HCID 21699942, compound

HRID 1597341Notes

Reaction equation

HRID 1597341 reaction equation
[H-].[Na+].CN(C)C=[O:6].[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=O)[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([S:24][CH3:25])=[CH:20][CH:19]=2)=[CH:12][CH:11]=1.Br[CH2:28][C:29](=[O:31])C>C(OCC)(=O)C>[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]([C:29](=[O:31])[CH3:28])[C:17]([C:18]2[CH:23]=[CH:22][C:21]([S:24][CH3:25])=[CH:20][CH:19]=2)=[O:6])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11715BromoacetoneHCID 24758Sodium hydrideHCID 544855161-(4-Methoxyphenyl)-2-[4-(methylsulfanyl)phenyl]ethan-1-one

Product 1

HCID 21699942HCID 21699942, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

0.44g (11.0 mol) of 60% sodium hydride was added to 27 ml of N,N-dimethylformamide solution containing 2.72 g (10.0 mmol) of 1-(4-methoxyphenyl)-2-(4-methylthiophenyl)ethanone, and stirred at the room temperature for 30 minutes, then 1.51 g (11.0 mol) of bromoacetone was added and further stirred at room temperature for 1 hour. 400 ml of ethyl acetate was added thereto and the mixture was washed three times with 200 ml of saturated saline. The organic layer was dried over anhydrous magnesium sulfate, then concentrated under reduced pressure followed by subjected to chromatography on silica gel (hexane:ethyl acetate=4:1) to obtain 2.27 g of 2-(4-methoxyphenyl)-1-(4-methylthiophenyl)butane-1,3-dion as colorless oil (yield: 69%).

Workup

  1. stirringfurther stirred at room temperature for 1 hour
  2. washthe mixture was washed three times with 200 ml of saturated saline
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-03c72e7b32414b9e9f48bc9889806b54
Source dataset
uspto-grants-2001_09
Patent number
US06294568B1

Reaction notes

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