Sodium hydride → 2-((3,3-Diphenylpropyloxy)methyl)-7-methoxybenzofuran

HRID 430785Notes

Reaction equation

HRID 430785 reaction equation
[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8][CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:19][O:20][C:21]1[C:29]2[O:28][C:27]([CH2:30]Cl)=[CH:26][C:25]=2[CH:24]=[CH:23][CH:22]=1.[Cl-].[NH4+]>O.CN(C=O)C>[C:11]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][CH2:9][O:10][CH2:30][C:27]2[O:28][C:29]3[C:21]([O:20][CH3:19])=[CH:22][CH:23]=[CH:24][C:25]=3[CH:26]=2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 299083,3-DiphenylpropanolHCID 183517417-Methoxy-2-chloromethylbenzofuran

Product 1

HCID 183517792-((3,3-Diphenylpropyloxy)methyl)-7-methoxybenzofuranYield 83.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3,3-diphenylpropanol (324 mg) and sodium hydride (60% dispersion in mineral oil, 54 mg) were added to DMF (5 ml) and the obtained mixture was stirred at room temperature for 15 minutes. 7-methoxy-2-chloromethylbenzofuran (250 mg) was then added and the resulting mixture was stirred at room temperature for 3 hours. The reaction mixture was added to saturated aqueous ammonium chloride solution (15 ml) to neutralize the mixture. Distilled water (20 ml) was added to the mixture and the resultant was extracted with 20 ml of ethyl acetate containing 15% of n-hexane three times. The organic layers were combined and washed with distilled water (10 ml) and with saturated brine (10 ml), followed by drying over anhydrous sodium sulfate. After removing the sodium sulfate by filtration, the solvent was removed under reduced pressure to dry the residue and the residue was purified by column chromatography (solvent: n-hexane/ethyl acetate=10/1) using silica gel to obtain the desired compound (394 mg, yield: 83%).

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 3 hours
  2. extractionthe resultant was extracted with 20 ml of ethyl acetate containing 15% of n-hexane three times
  3. washwashed with distilled water (10 ml) and with saturated brine (10 ml)
  4. dry with materialby drying over anhydrous sodium sulfate
  5. customAfter removing the sodium sulfate
  6. filtrationby filtration
  7. customthe solvent was removed under reduced pressure
  8. customto dry the residue
  9. customthe residue was purified by column chromatography (solvent: n-hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-3a417d540d6443e684f0497b226e685b
Source dataset
uspto-grants-2001_11
Patent number
US06323235B1

Reaction notes

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