Water → [4-(1,3-Oxazol-5-yl)phenyl]methanol

HRID 910231Notes

Reaction equation

HRID 910231 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]1[C:11]([C:12]2[CH:21]=[CH:20][C:15]([C:16](OC)=[O:17])=[CH:14][CH:13]=2)=[CH:10][N:9]=[CH:8]1.F.O>O1CCCC1>[O:7]1[C:11]([C:12]2[CH:13]=[CH:14][C:15]([CH2:16][OH:17])=[CH:20][CH:21]=2)=[CH:10][N:9]=[CH:8]1

Participants

6

Reactant 4

HCID 962WaterHCID 14917Hydrofluoric AcidHCID 1477779Methyl 4-(1,3-oxazol-5-yl)benzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 45588265[4-(1,3-Oxazol-5-yl)phenyl]methanolYield 36.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution (2.08 mL) of lithium aluminum hydride (2.4 mole) in tetrahydrofuran was added dropwise under ice cooling to a solution of methyl 4-(1,3-oxazol-5-yl)benzoate (1.02 g) in tetrahydrofuran (20 mL), followed by stirring at 0° C. for 30 minutes. Hydrogen fluoride (840 mg) and water (270 mL) were added to the solution, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified through flash column chromatography (n-hexane:ethyl acetate=3:2), followed by concentration under reduced pressure, to thereby yield the title compound (321 mg).

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified through flash column chromatography (n-hexane:ethyl acetate=3:2)
  5. concentrationfollowed by concentration under reduced pressure

Sources & evidence

ORD record
ord-193ff042b3504625b439deeb0bbf807a
Source dataset
uspto-grants-2011_09
Patent number
US08022075B2

Reaction notes

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