Triethylamine → 1-[4,5-Bis(4-methylphenyl)oxazol-2-yl)butan-1,4-dione

HRID 380149

Reaction equation

HRID 380149 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[O:8][C:9]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[N:11]=1)=[O:6].C(N(CC)CC)C.N1C=CC=CC=1S(O)(=O)=O>CS(C)=O>[CH3:18][C:15]1[CH:14]=[CH:13][C:12]([C:10]2[N:11]=[C:7]([C:5](=[O:6])[CH2:4][CH2:3][CH:2]=[O:1])[O:8][C:9]=2[C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 948492-Pyridinesulfonic acidHCID 183673354-Hydroxy-1-(4,5-bis(4-methylphenyl)-oxazol-2-yl)butan-1-one

Product 1

HCID 183673471-[4,5-Bis(4-methylphenyl)oxazol-2-yl)butan-1,4-dioneYield 28.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a solution of 4-hydroxy-1-(4,5-bis(4-methylphenyl)-oxazol-2-yl)butan-1-one (0.78 g) and triethylamine (2 ml) in DMSO (10 ml) was added a solution of pyridinesulfonic acid (1.16 g) in DMSO (4 ml) at room temperature. After being stirred for 20 minutes at the same temperature, the mixture was partitioned between ethyl acetate and water. The organic layer was washed with 1M-HCl, water and brine. The dried solvent was evaporated in vacuo and the residue was purified by chromatography on silica gel to give 1-[4,5-bis(4-methylphenyl)oxazol-2-yl)butan-1,4-dione (0.22 g).

Workup

  1. customthe mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with 1M-HCl, water and brine
  3. customThe dried solvent was evaporated in vacuo
  4. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-85234cc419fd4bc8ac2604859cdfc4e9
Source dataset
uspto-grants-2001_10
Patent number
US06300344B1

Linked notes

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