Water → HCID 9837611, compound

HRID 2255242Notes

Reaction equation

HRID 2255242 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH2:13][CH2:14][C:15](O)=[O:16])[O:11][CH:12]=2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([CH2:13][CH2:14][CH2:15][OH:16])[O:11][CH:12]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 18953969HCID 18953969, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 9837611HCID 9837611, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(4-chlorophenyl)-2-oxazoleproponic acid (1.5 g) in THF (20 ml) was added lithium aluminum hydride (0.27 g), followed by stirring for 3 hours at room temperature. Water (3 ml) was added to the reaction mixture. The resultant was extracted with ethyl acetate. The ethyl acetate layer was washed with 2N-HCl and water, dried over MgSO4, and distilled to remove the solvent. The oily residue was subjected to a silica gel chromatography. Crystals of 3-[4-(4-chlorophenyl)-2-oxazolyl]propanol (1.11 g, 78%) were obtained from the fraction eluted with ethyl acetate-hexane (2:1, V/V). Recrystallization from ether-hexane gave colorless prism crystals of mp 43°-44° C.

Workup

  1. extractionThe resultant was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with 2N-HCl and water
  3. dry with materialdried over MgSO4
  4. distillationdistilled
  5. customto remove the solvent

Sources & evidence

ORD record
ord-46daca24fb6a44bd8257521ed684a934
Source dataset
uspto-grants-1993_08
Patent number
US05239080

Reaction notes

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