Reacción #595340

ord-1416c1ca9a0c43d886b805592fc7c512

Ecuación de reacción

[Al+3].[H-].[H-].[H-].[H-].[Li+]
lithium aluminum hydride
CCOC(=O)c1coc(-c2ccc(Cl)c(C)c2)n1
compound
CCOC(=O)c1coc(-c2ccc(Cl)c(C)c2)n1
Ethyl 2-(4-chloro-3-methylphenyl)-1,3-oxazole-4-carboxylate
O
water
[Na+].[OH-]
sodium hydroxide
Cc1cc(-c2nc(CO)co2)ccc1Cl
[2-(4-Chloro-3-methylphenyl)-1,3-oxazol-4-yl]methanol

Disolventes

Condiciones de reacción

Temperatura
0°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    TemperaturaThe reaction solution is then once more cooled to 0° C.
  2. 2
    workup.STIRRINGThe mixture is stirred at RT overnight
  3. 3
    OtroThe precipitate formed
  4. 4
    Filtraciónis filtered off
  5. 5
    Otroa rotary evaporator
  6. 6
    OtroThe residue is used without further purification in the subsequent reaction

Procedimiento

46 mg (1.22 mmol) of lithium aluminum hydride are initially charged in 8.0 ml of THF and cooled to 0° C. A solution of 161 mg (0.61 mmol) of the compound from Example 26A in 2.5 ml of THF is then added dropwise. The mixture is stirred at RT for 2 h. The reaction solution is then once more cooled to 0° C., and 0.2 ml of water and 0.4 ml of 1 N aqueous sodium hydroxide solution are added. The mixture is stirred at RT overnight. The precipitate formed is filtered off, and the filtrate is freed from the solvent using a rotary evaporator. The residue is used without further purification in the subsequent reaction.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09095582B2uspto-grants-2015_08