Potassium Carbonate → 5-(2-Pyridyl)oxazole

HRID 1775507Notes

Reaction equation

HRID 1775507 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=[O:8].CC1C=CC(S([CH2:19][N+:20]#[C-:21])(=O)=O)=CC=1.C([O-])([O-])=O.[K+].[K+]>CO>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[O:8][CH:21]=[N:20][CH:19]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 142732-PyridinecarboxaldehydeHCID 161915Tosylmethyl isocyanide

Product 1

HCID 7371945-(2-Pyridyl)oxazoleYield 49%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of picolinaldehyde (2.3 g, 42.6 mmol), TosMIC (4.4 g, 45.2 mmol) and K2CO3 (3.4 g, 48.8 mmol) in methanol (70 mL) was reflux for 2 h. The reaction was cooled to room temperature, then the mixture was concentrated and purified by silica gel column chromatography to give the desired product (3.05 g).

Workup

  1. temperaturewas reflux for 2 h
  2. concentrationthe mixture was concentrated
  3. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-e23ed6dffdfc4e67bbfa3eac5dfff501
Source dataset
uspto-grants-2016_02
Patent number
US09260452B2

Reaction notes

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