Ethyl Acetate → HCID 59594660, compound

HRID 2263378Notes

Reaction equation

HRID 2263378 reaction equation
C([O:3][C:4]([C:6]1[O:10][C:9]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)=[N:8][C:7]=1[CH3:23])=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.[NH4+].[Cl-]>O1CCCC1>[CH3:23][C:7]1[N:8]=[C:9]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:20])[F:21])=[CH:15][CH:14]=2)[O:10][C:6]=1[CH2:4][OH:3]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 59594721HCID 59594721, compound

Product 1

HCID 59594660HCID 59594660, compoundYield 49.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

9.70 g 4-Methyl-2-[2-(4-trifluoromethyl-phenyl)-ethyl]-oxazole-5-carboxylic acid ethyl ester were dissolved in 20 ml tetrahydrofuran and added to a ice cooled solution of 1.13 g lithium aluminium hydride in 10 ml tetrahydrofuran. The reaction mixture was stirred at 0° C. for one hour. Then 100 ml ethyl acetate and 50 ml saturated NH4Cl solution were added. The precipitate was filtered off through a celite pad and washed with ethyl acetate. The organic layer of the filtrate was separated. The aqueous layer of the filtrate was extracted two times with portions of 100 ml ethyl acetate. The combined organic layers were dried over MgSO4. The solvent was removed in vacuo and the residue purified by chromatography on silica gel with the eluent petroleum benzene:ethyl acetate=1:1 to obtain to 4.20 g {4-methyl-2-[2-(4-trifluoromethyl-phenyl)-ethyl]-oxazol-5-yl}-methanol a yellow solid.

Workup

  1. filtrationThe precipitate was filtered off through a celite pad
  2. washwashed with ethyl acetate
  3. customThe organic layer of the filtrate was separated
  4. extractionThe aqueous layer of the filtrate was extracted two times with portions of 100 ml ethyl acetate
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. customThe solvent was removed in vacuo
  7. customthe residue purified by chromatography on silica gel with the eluent petroleum benzene

Sources & evidence

ORD record
ord-c289d6a71eff4d029ac18c66ee74ca59
Source dataset
uspto-grants-2010_12
Patent number
US07851493B2

Reaction notes

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