Potassium Hydroxide → 4-[2-(Indan-4-yloxy)-ethyl]-5-methyl-2-phenyl-oxazole

HRID 479156Notes

Reaction equation

HRID 479156 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15]S(C)(=O)=O.[CH2:20]1[C:28]2[CH:27]=[CH:26][CH:25]=[C:24](O)[C:23]=2[CH2:22][CH2:21]1.[OH-].[K+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.O>[CH2:20]1[C:28]2[C:23](=[C:24]([O:15][CH2:14][CH2:13][C:3]3[N:4]=[C:5]([C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=4)[O:6][C:2]=3[CH3:1])[CH:25]=[CH:26][CH:27]=2)[CH2:22][CH2:21]1

Participants

7

Reactant 3

HCID 14797Potassium HydroxideHCID 742334-HydroxyindanHCID 105407732-(5-Methyl-2-phenyl-1,3-oxazol-4-yl)ethyl methanesulfonate

Product 1

HCID 180035744-[2-(Indan-4-yloxy)-ethyl]-5-methyl-2-phenyl-oxazoleYield 107.9%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

4.00 g of methanesulfonic acid 2-(5-methyl-2-phenyl-oxazol-4-yl)-ethyl ester [PCT Int. Appl. (2000) WO0008002] (14.22 mmol), 2.00 g of 4-indanol (14.93 mmol) and 487.6 mg of tetrabutylammonium hydrogen sulfate were dissolved in 65 ml of toluene and heated to 80° C. KOH was then slowly added (10.66 ml of a 2M solution in H2O, 21.33 mmol), keeping the temperature at 75-80° C. The resulting mixture was stirred for 4 hours at 80° C. 35 ml of water were added, the mixture stirred for another 5 minutes at 80° C. and the water phase was then removed. 20 ml of water were added to the toluene phase, the mixture stirred for 5 minutes at 80° C., and the water phase removed. The water phase was extracted 3 times with dichloromethane. The combined organic phases were dried over MgSO4 and evaporated to afford 4.90 g (100%) of 4-[2-(indan-4-yloxy)-ethyl]-5-methyl-2-phenyl-oxazole as brown solid.

Workup

  1. customat 75-80° C
  2. stirringthe mixture stirred for another 5 minutes at 80° C.
  3. customthe water phase was then removed
  4. addition20 ml of water were added to the toluene phase
  5. stirringthe mixture stirred for 5 minutes at 80° C.
  6. customthe water phase removed
  7. extractionThe water phase was extracted 3 times with dichloromethane
  8. dry with materialThe combined organic phases were dried over MgSO4
  9. customevaporated

Sources & evidence

ORD record
ord-4189de0efefd48ba9768d70f5335262b
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Reaction notes

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