Potassium Carbonate → 5-(2-Methoxyphenyl)-1,3-oxazole

HRID 1023876Notes

Reaction equation

HRID 1023876 reaction equation
CO[C:3]1[CH:4]=[CH:5][C:6]([CH:9]=[O:10])=[CH:7][CH:8]=1.[C:11]([O-:14])([O-])=O.[K+].[K+].CC1C=CC(S([CH2:27][N+:28]#[C-:29])(=O)=O)=CC=1>CO>[CH3:11][O:14][C:7]1[CH:8]=[CH:3][CH:4]=[CH:5][C:6]=1[C:9]1[O:10][CH:29]=[N:28][CH:27]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 312444-MethoxybenzaldehydeHCID 161915Tosylmethyl isocyanide

Product 1

HCID 167406765-(2-Methoxyphenyl)-1,3-oxazoleYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
80 °C

Procedure

To a solution of Anisaldehyde (2.0 mmol) in MeOH (5.0 mL), was added K2CO3 (2.2 mmol) and TOSMIC (1.10 mmol) and the reaction was allowed to stir at 80° C. in a sealed vial. After the reaction was over, the methanol was removed and the crude product was absorbed in silica gel and purified by column chromatography. The product was isolated in 83% yield as colorless oil. 1H NMR: 3.91 (s, 3H), 6.94 (d, 1H, J=8.4 Hz), 7.01 (t, 1H, J=7.6 Hz), 6.94 (t, 1H, J=8.4 Hz), 7.53 (s, 1H), 7.75 (d, 1H, J=8.0 Hz), 7.53 (s, 1H).

Workup

  1. customwas removed
  2. customthe crude product was absorbed in silica gel
  3. custompurified by column chromatography
  4. customThe product was isolated in 83% yield as colorless oil

Sources & evidence

ORD record
ord-1581a934d57c46999e44e8ed2b0100f0
Source dataset
uspto-grants-2014_05
Patent number
US08722720B2

Reaction notes

Loading…