Triethylamine → 1-[4-(Methylsulfonyl)phenyl]-3-methylpentane-1,4-dione

HRID 497178

Reaction equation

HRID 497178 reaction equation
[CH3:1][S:2]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH3:13][C:14](=[CH2:18])[C:15](=[O:17])[CH3:16].CCN(CC)CC>C(O)C.[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1>[CH3:1][S:2]([C:5]1[CH:12]=[CH:11][C:8]([C:9](=[O:10])[CH2:13][CH:14]([CH3:18])[C:15](=[O:17])[CH3:16])=[CH:7][CH:6]=1)(=[O:3])=[O:4]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 13143Methyl isopropenyl ketoneHCID 2203764-(Methylsulfonyl)benzaldehyde

Product 1

HCID 218628391-[4-(Methylsulfonyl)phenyl]-3-methylpentane-1,4-dioneYield 4.3%

Reagents, catalysts & solvents 2

HCID 28333523-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chlorideCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of 4-(methylsulfonyl)benzaldehyde (1.84 g, 10 mmol) in ethanol (8 mL) was added 3-methyl-3-buten-2-one (0.8 g, 9.5 mmol), 3-benzyl-5-(2-hydroxyethyl)4-methylthiazolium chloride (0.51 g, 1.9 mmol), and Et3N (2.65 mL, 19 mmol) at room temperature. After stirring for 3 hours, volatiles were removed by evaporation. The residue was purified by flash chromatography on silica gel eluting with ethyl acetate/hexane (1/2) to provide the subtitle compound (0.11 g).

Workup

  1. customvolatiles were removed by evaporation
  2. customThe residue was purified by flash chromatography on silica gel eluting with ethyl acetate/hexane (1/2)

Sources & evidence

ORD record
ord-e10ed4ece8f342968dfb5394edfe7316
Source dataset
uspto-grants-2005_09
Patent number
US06949536B2

Linked notes

Loading…