Water → HCID 18351869, compound

HRID 430741Notes

Reaction equation

HRID 430741 reaction equation
Br[CH2:2][C:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[C:11]([O:12][CH3:13])[C:6]=2[O:5][CH:4]=1.[N-:14]=[N+:15]=[N-:16].[Na+].O>CO.O>[N:14]([CH2:2][C:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[C:11]([O:12][CH3:13])[C:6]=2[O:5][CH:4]=1)=[N+:15]=[N-:16]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 18351867HCID 18351867, compound

Product 1

HCID 18351869HCID 18351869, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

3-bromomethyl-7-methoxybenzofuran (565 mg) and sodium azide (230 mg) were dissolved in methanol-water (5:1, 10 ml) and the solution was refluxed for 1 hour. After cooling the reaction solution to room temperature, the reaction solution was poured into water layer (30 ml) and extracted twice with ethyl acetate (20 ml). The organic layers were combined and washed with saturated brine, followed by drying the resultant over sodium sulfate. After removing sodium sulfate, the solvent was removed under reduced pressure and the residue was purified by column chromatography (solvent: hexane/ethyl acetate=9/1) using silica gel to obtain the desired compound (452 mg, yield: 95%).

Workup

  1. temperaturethe solution was refluxed for 1 hour
  2. extractionextracted twice with ethyl acetate (20 ml)
  3. washwashed with saturated brine
  4. dry with materialby drying the resultant over sodium sulfate
  5. customAfter removing sodium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customthe residue was purified by column chromatography (solvent: hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-47e20373bd244caba3f50de177e65c86
Source dataset
uspto-grants-2001_11
Patent number
US06323235B1

Reaction notes

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