Triethylamine → HCID 67546943, compound

HRID 2356753Notes

Reaction equation

HRID 2356753 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([C:10]([OH:12])=O)[CH:8]=[CH:9][C:2]1=2.[N+:13]([CH2:15][C:16]([O:18][CH3:19])=[O:17])#[C-:14].P(C#N)(OCC)(OCC)=O.C(N(CC)CC)C>CN(C)C=O>[O:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([C:10]3[O:12][CH:14]=[N:13][C:15]=3[C:16]([O:18][CH3:19])=[O:17])[CH:8]=[CH:9][C:2]1=2

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 547815Methyl isocyanoacetateHCID 5956561-Benzofuran-5-Carboxylic Acid

Product 1

HCID 67546943HCID 67546943, compoundYield 58.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of benzo[b]furan-5-carboxylic acid (1.30 g) and of methyl isocyanoacetate (834 mg) in N,N-dimethylformamide (10 ml) were added diethyl cyanophosphate (1.33 ml) and triethylamine (3.6 ml) at room temperature, and the mixture was stirred overnight. After removing the solvent under reduced pressure, an aqueous citric acid solution and ethyl acetate were added to the residue, the organic layer was collected, washed successively with an aqueous citric acid solution, water, a saturated aqueous sodium hydrogen carbonate solution and brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography (solvent: n-hexane:ethyl acetate=1:1) to obtain a crude product of methyl 5-(5-benzo[b]furyl)oxazol-4-carboxylate (1.14 g).

Workup

  1. customAfter removing the solvent under reduced pressure
  2. additionan aqueous citric acid solution and ethyl acetate were added to the residue
  3. customthe organic layer was collected
  4. washwashed successively with an aqueous citric acid solution, water
  5. dry with materiala saturated aqueous sodium hydrogen carbonate solution and brine, dried over anhydrous sodium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (solvent: n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-626d9e8b85eb4768b40d572f15e781e7
Source dataset
uspto-grants-2010_07
Patent number
US07759373B2

Reaction notes

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