Water → [5-(4-Chlorophenyl)-1,3-oxazol-4-yl]methanol

HRID 508164Notes

Reaction equation

HRID 508164 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:18][CH:17]=[N:16][C:15]=2[C:19](OC)=[O:20])=[CH:10][CH:9]=1.O.[OH-].[Na+]>C1COCC1>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[O:18][CH:17]=[N:16][C:15]=2[CH2:19][OH:20])=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 118463424-Oxazolecarboxylic acid, 5-(4-chlorophenyl)-, methyl esterHCID 21226445Aluminium lithium hydride

Product 1

HCID 58284362[5-(4-Chlorophenyl)-1,3-oxazol-4-yl]methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

166 mg (4.38 mmol) of lithium aluminum hydride are initially charged in 10 ml of dry THF and cooled to 0° C. A solution of 260 mg (1.09 mmol) of the compound from Example 37A in 10 ml of dry THF is added dropwise. After the addition has ended, the reaction solution is slowly warmed to RT and stirred at this temperature for 1 h. With stirring, the mixture is then heated at reflux for 2 h. The mixture is then cooled again to 0° C., 0.4 ml of water and 0.8 ml of 1 N aqueous sodium hydroxide solution are added carefully and the mixture is stirred at RT for 3 h. The precipitate formed is filtered off, and the filtrate is freed from the solvent on a rotary evaporator. The residue is used without further purification in the subsequent reaction.

Workup

  1. additionAfter the addition
  2. temperaturethe reaction solution is slowly warmed to RT
  3. stirringWith stirring
  4. temperaturethe mixture is then heated
  5. temperatureat reflux for 2 h
  6. temperatureThe mixture is then cooled again to 0° C.
  7. stirringthe mixture is stirred at RT for 3 h
  8. customThe precipitate formed
  9. filtrationis filtered off
  10. customthe filtrate is freed from the solvent on a rotary evaporator
  11. customThe residue is used without further purification in the subsequent reaction

Sources & evidence

ORD record
ord-a7fa4604d7d7428d90a722e1774742b3
Source dataset
uspto-grants-2015_08
Patent number
US09095582B2

Reaction notes

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