Potassium Carbonate → 2-[1,3]Dioxolan-2-yl-6-oxazol-5-yl-pyridine

HRID 376293Notes

Reaction equation

HRID 376293 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[N:11]=[C:10]([CH:12]=[O:13])[CH:9]=[CH:8][CH:7]=1.S([CH2:24][N:25]=[C:26]=O)(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CO>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:7]=[CH:8][CH:9]=[C:10]([C:12]2[O:13][CH:26]=[N:25][CH:24]=2)[N:11]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 117890781-Isocyanatomethanesulfonyl-4-methylbenzeneHCID 193617196-[1,3]Dioxolan-2-yl-pyridine-2-carbaldehyde

Product 1

HCID 105607472-[1,3]Dioxolan-2-yl-6-oxazol-5-yl-pyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1 g of 6-[1,3]dioxolan-2-yl-pyridine-2-carbaldehyde (5.58 mmol), 1.10 g of tosylmethyl isocyanate (5.63 mmol) and 0.80 g of potassium carbonate (5.79 mmol) are mixed in 15 ml of methanol. The suspension is heated under reflux for 2 hours. The methanol is separated off, the residue is taken up in a saturated aqueous solution of sodium chloride and the mixture is extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and then concentrated under vacuum. The title product is isolated by chromatography on a silica column (eluent: hexane/ethyl acetate; 50:50). 1.14 g of a yellow oil are obtained.

Workup

  1. temperatureThe suspension is heated
  2. temperatureunder reflux for 2 hours
  3. customThe methanol is separated off
  4. extractionthe mixture is extracted with ethyl acetate
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-4086eb7de1be46608c105d917d10e42e
Source dataset
uspto-grants-2000_02
Patent number
US06020345

Reaction notes

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