Acetic Acid → 3-(2-(4-Phenylbenzyloxy)ethyl)-7-methoxybenzofuran

HRID 430783Notes

Reaction equation

HRID 430783 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[C:12]([O:13][CH3:14])[C:7]=2[O:6][CH:5]=1.CC(C)([O-])C.[K+].[C:21]1([C:27]2[CH:34]=[CH:33][C:30]([CH2:31]Cl)=[CH:29][CH:28]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(O)(=O)C>CN(C=O)C.O>[C:21]1([C:27]2[CH:28]=[CH:29][C:30]([CH2:31][O:1][CH2:2][CH2:3][C:4]3[C:8]4[CH:9]=[CH:10][CH:11]=[C:12]([O:13][CH3:14])[C:7]=4[O:6][CH:5]=3)=[CH:33][CH:34]=2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 154634-Phenylbenzyl chlorideHCID 226629353-(2-Hydroxyethyl)-7-methoxybenzofuranHCID 23665647Potassium tert-butoxide

Product 1

HCID 183515903-(2-(4-Phenylbenzyloxy)ethyl)-7-methoxybenzofuranYield 88.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3-(2-hydroxyethyl)-7-methoxybenzofuran (373 mg) was dissolved in DMF (7 ml) and potassium t-butoxide (261 mg) was added to the obtained solution, followed by stirring the resulting solution at room temperature for 20 minutes. To this reaction solution, 4-phenylbenzyl chloride (511 mg) was added and the solution was stirred at room temperature for 1 hour. Acetic acid was added to the reaction solution and the resultant was poured into water layer (50 ml), followed by extraction twice with ethyl acetate (20 ml). The organic layers were combined and washed with saturated brine, followed by drying over sodium sulfate. After removing the sodium sulfate by filtration, the solvent was removed under reduced pressure and the residue was purified by column chromatography (solvent: hexane/ethyl acetate=5/1) using silica gel to obtain the desired compound (613 mg, yield: 88%).

Workup

  1. stirringthe solution was stirred at room temperature for 1 hour
  2. extractionfollowed by extraction twice with ethyl acetate (20 ml)
  3. washwashed with saturated brine
  4. dry with materialby drying over sodium sulfate
  5. customAfter removing the sodium sulfate
  6. filtrationby filtration
  7. customthe solvent was removed under reduced pressure
  8. customthe residue was purified by column chromatography (solvent: hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-c18d807010494733bd99f084bdb4fdc7
Source dataset
uspto-grants-2001_11
Patent number
US06323235B1

Reaction notes

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