HCID 57554698, compound → HCID 28293537, compound

HRID 1511876Notes

Reaction equation

HRID 1511876 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][C:12]1[O:13][C:14]([CH3:17])=[CH:15][N:16]=1)C1C=CC=CC=1>C(O)C.[Pd]>[CH3:17][C:14]1[O:13][C:12]([CH2:11][CH2:10][CH2:9][OH:8])=[N:16][CH:15]=1

Participants

4

Reactant 1

HCID 57554698HCID 57554698, compound

Product 1

HCID 28293537HCID 28293537, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-(3-Benzyloxy-propyl)-5-methyl-oxazole (675 mg, 2.92 mmol) in ethanol (15 ml) containing a suspension of 10% Pd on C (63.9 mg, 0.06 mmol) was hydrogenated overnight at room temperature. The catalyst was removed by filtration through Celite®, then the filtrate was concentrated and the residue was purified on silica gel using 1:1/heptane:ethyl acetate and then ethyl acetate as eluants. Fractions that contained product were combined and concentrated under reduced pressure to yield 3-(5-Methyl-oxazol-2-yl)-propan-1-ol (242 mg, 59%) as an oil.

Workup

  1. customThe catalyst was removed by filtration through Celite®
  2. concentrationthe filtrate was concentrated
  3. customthe residue was purified on silica gel using 1:1/heptane
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ff2d7b1adb7842ba91dfb941744f8d42
Source dataset
uspto-grants-2012_07
Patent number
US08217027B2

Reaction notes

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