Potassium Carbonate → HCID 69201641, compound

HRID 2117648Notes

Reaction equation

HRID 2117648 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:11]([O-:13])=[O:12])=[C:7]([CH:10]=1)[CH:8]=[O:9].S([CH2:24][N+:25]#[C-:26])(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:11]([O-:13])=[O:12])=[C:7]([C:8]2[O:9][CH:26]=[N:25][CH:24]=2)[CH:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 2303715-Methoxy-2-nitrobenzaldehyde

Product 1

HCID 69201641HCID 69201641, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 5-methoxy-2-nitro-benzaldehyde (3.5 g, 19.3 mmol), tosylmethyl-isocyanide (4.5 g, 23.05 mmol) and potassium carbonate (6.7 g, 48.5 mmol) in methanol (40 mL) was stirred at room temperature for 4 h. The resulting red-orange suspension was concentrated and the residue diluted with ethyl acetate. The mixture was partitioned between ethyl acetate and water. The organic phase was separated and washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated to afford a yellow oil. This oil was purified via column chromatography on silica gel (gradient elution with 0-10% methanol-methylenechloride) to afford 5-(5-methoxy-2-nitrophenyl)oxazole.

Workup

  1. concentrationThe resulting red-orange suspension was concentrated
  2. additionthe residue diluted with ethyl acetate
  3. customThe mixture was partitioned between ethyl acetate and water
  4. customThe organic phase was separated
  5. washwashed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto afford a yellow oil
  10. customThis oil was purified via column chromatography on silica gel (gradient elution with 0-10% methanol-methylenechloride)

Sources & evidence

ORD record
ord-5f67ed47b1a244e19d1076ccbe0fde4a
Source dataset
uspto-grants-2008_10
Patent number
US07442698B2

Reaction notes

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