HCID 49372722, compound → HCID 57554698, compound

HRID 1511875Notes

Reaction equation

HRID 1511875 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]([NH:14][CH2:15][C:16]#[CH:17])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(#N)C.[Au](Cl)(Cl)Cl>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]1[O:13][C:16]([CH3:17])=[CH:15][N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 49372722HCID 49372722, compound

Product 1

HCID 57554698HCID 57554698, compoundYield 81.1%

Reagents, catalysts & solvents 2

HCID 26030Gold trichlorideCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 4-Benzyloxy-N-prop-2-ynyl-butyramide (500 mg, 2.16 mmol) in acetonitrile (22 ml) was treated with Gold (III) chloride (32.8 mg, 0.108 mmol) at room temperature. The reaction was heated at 50° C. for 8 hours then was allowed to stir at room temperature overnight. The reaction was concentrated under reduced pressure and the residue was purified on silica gel using 1:1/heptane:ethyl acetate as eluant. Fractions that contained product were combined and concentrated under reduced pressure to yield 2-(3-Benzyloxy-propyl)-5-methyl-oxazole (405 mg, 81%) as a clear oil.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customthe residue was purified on silica gel using 1:1/heptane
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6c28dd14d3d8493bbde4e2efa34be45d
Source dataset
uspto-grants-2012_07
Patent number
US08217027B2

Reaction notes

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