Sodium Hydroxide → 2-[2-(4-Fluorophenyl)-5-methyloxazol-4-yl]ethanol

HRID 526798Notes

Reaction equation

HRID 526798 reaction equation
C([O:9][CH2:10][CH2:11][C:12]1[N:13]=[C:14]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[O:15][C:16]=1[CH3:17])(=O)C1C=CC=CC=1.[OH-].[Na+]>C(O)C>[F:24][C:21]1[CH:20]=[CH:19][C:18]([C:14]2[O:15][C:16]([CH3:17])=[C:12]([CH2:11][CH2:10][OH:9])[N:13]=2)=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 866806502-[2-(4-Fluorophenyl)-5-methyloxazol-4-yl]ethyl benzoate

Product 1

HCID 107989992-[2-(4-Fluorophenyl)-5-methyloxazol-4-yl]ethanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The intermediate, 2-[2-(4-fluorophenyl)-5-methyloxazol-4-yl]ethyl benzoate (19.5 g, 60 mmol) was dissolved in 70 ml ethanol and stirred. 10% sodium hydroxide solution (NaOH: 4.8 g, 120 mmol) was slowly added dropwise, and the mixture was stirred overnight at room temperature. After the reaction was completed, the ethanol was concentrated, and the product was extracted with toluene, and then was washed with water and brine sequently, dried with anhydrous magnesium sulfate, and concentrated to obtain the intermediate, i.e. 2-[2-(4-fluorophenyl)-5-methyloxazol-4-yl]ethanol, which was directly applied in the next step without further purification.

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. concentrationthe ethanol was concentrated
  3. extractionthe product was extracted with toluene
  4. washwas washed with water and brine sequently
  5. dry with materialdried with anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e41d0f3f52484536b97f95621bd6ca11
Source dataset
uspto-grants-2016_05
Patent number
US09346770B2

Reaction notes

Loading…