Hydrochloric Acid → 3-Ethyl-4-oxo-4-(2-phenyl-benzoxazol-6-yl)-butyric acid

HRID 1619945Notes

Reaction equation

HRID 1619945 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[C:11]1([C:17]2[O:18][C:19]3[CH:25]=[C:24]([C:26](=[O:30])[CH2:27][CH2:28][CH3:29])[CH:23]=[CH:22][C:20]=3[N:21]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C[O:32][C:33](=[O:36])[CH2:34]Br.Cl>C1(C)C=CC=CC=1.C1COCC1>[CH2:28]([CH:27]([C:26](=[O:30])[C:24]1[CH:23]=[CH:22][C:20]2[N:21]=[C:17]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[O:18][C:19]=2[CH:25]=1)[CH2:34][C:33]([OH:36])=[O:32])[CH3:29]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 60984Methyl bromoacetateHCID 3251421Potassium bis(trimethylsilyl)amideHCID 674660111-(2-Phenyl-benzoxazol-6-yl)butan-1-one

Product 1

HCID 674662343-Ethyl-4-oxo-4-(2-phenyl-benzoxazol-6-yl)-butyric acid

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

625.00 μl (313 μmol) potassium bis(trimethylsilyl)amide 0.5M in toluene are placed in 15 ml THF and cooled to −78° C. 75.00 mg (283 μmol) 1-(2-phenyl-benzoxazol-6-yl)-butan-1-one, dissolved in 15 ml THF, are added dropwise to this solution and the mixture is stirred for 15 min at −78° C. Then 55 mg (360 μmol) methylbromoacetate, dissolved in 5 ml THF, are also added dropwise and the mixture is stirred for 30 min at −78° C., then 1N hydrochloric acid is added and the mixture is extracted with diethyl ether. The org. phase is dried on magnesium sulphate and the solv. is eliminated i.V.

Workup

  1. additionare added dropwise to this solution
  2. additionare also added dropwise
  3. stirringthe mixture is stirred for 30 min at −78° C.
  4. extractionthe mixture is extracted with diethyl ether
  5. customphase is dried on magnesium sulphate

Sources & evidence

ORD record
ord-e10417453f1d4371aa095ac680b78911
Source dataset
uspto-grants-2014_07
Patent number
US08772323B2

Reaction notes

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