Potassium Carbonate → 4-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethoxy]benzothiophene

HRID 1449589Notes

Reaction equation

HRID 1449589 reaction equation
[OH:1][C:2]1[C:7]2[CH:8]=[CH:9][S:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH3:17][C:18]1[O:22][C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:20][C:19]=1[CH2:29][CH2:30]Br>CC(CC)=O>[CH3:17][C:18]1[O:22][C:21]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[N:20][C:19]=1[CH2:29][CH2:30][O:1][C:2]1[C:7]2[CH:8]=[CH:9][S:10][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 19217Benzo(b)thiophen-4-olHCID 156164424-(2-Bromoethyl)-5-methyl-2-phenyloxazole

Product 1

HCID 112329474-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethoxy]benzothiopheneYield 77.2%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

5.15 g (0.034 mol) 4-hydroxybenzothiophene was dissolved in 130 ml methylethylketone and admixed with 9.4 g (0.068 mol) K2CO3 and 20 g (0.068 mol) 5-methyl-2-phenyl-4-(2-bromoethyl)oxazole. The preparation was boiled for 72 hours under reflux, evaporated, taken up in ethyl acetate and extracted three times by shaking with 2N NaOH. After cooling and evaporation of the organic phase, it was crystallized from ethyl acetate/isohexane. 8.8 g 4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzothiophene of melting point 130°-132° C. is obtained.

Workup

  1. temperatureunder reflux
  2. customevaporated
  3. extractionextracted three times
  4. temperatureAfter cooling
  5. customevaporation of the organic phase, it
  6. customwas crystallized from ethyl acetate/isohexane

Sources & evidence

ORD record
ord-07a8b3b357c348039bedb8ad5344d17d
Source dataset
uspto-grants-1997_02
Patent number
US05599826

Reaction notes

Loading…