Water → HCID 86678202, compound

HRID 1747548Notes

Reaction equation

HRID 1747548 reaction equation
[CH2:1]([O:3][CH:4]([O:13][CH2:14][CH3:15])[C:5]1[CH:6]=[CH:7][C:8]([CH:11]=[O:12])=[N:9][CH:10]=1)[CH3:2].C1(C)C=CC(S([CH2:25][N+:26]#[C-:27])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].O>CO>[CH2:14]([O:13][CH:4]([O:3][CH2:1][CH3:2])[C:5]1[CH:6]=[CH:7][C:8]([C:11]2[O:12][CH:27]=[N:26][CH:25]=2)=[N:9][CH:10]=1)[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 86678201HCID 86678201, compound

Product 1

HCID 86678202HCID 86678202, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In methanol (5 mL) was dissolved 5-(diethoxymethyl)picolinaldehyde (148 mg, 0.707 mmol) obtained in Step 1. To the solution were added toluene-4-sulfonylmethylisocyanide (345 mg, 1.77 mmol) and potassium carbonate (244 mg, 1.77 mmol) and the mixture was stirred at room temperature for 8 hours. Water was added to the reaction mixture. Extraction with ethyl acetate, washing with saturated brine and drying over anhydrous sodium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/3) to give 5-(5-(diethoxymethyl)pyridin-2-yl)oxazole (161 mg, 92% yield).

Workup

  1. extractionExtraction with ethyl acetate
  2. washwashing with saturated brine
  3. dry with materialdrying over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. customthe solvent in the filtrate was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/3)

Sources & evidence

ORD record
ord-d81347b6e8e84e81aefeab56071ea9d9
Source dataset
uspto-grants-2015_10
Patent number
US09150569B2

Reaction notes

Loading…