Dimethylformamide → Methyl 6-(phenylmethoxy)-2-benzofurancarboxylate

HRID 1357188Notes

Reaction equation

HRID 1357188 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:5]2[CH:6]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[O:8][C:4]=2[CH:3]=1.[H-].[Na+].CN(C=O)C.[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1.CCOC(C)=O.O>[CH2:22]([O:1][C:2]1[CH:14]=[CH:13][C:5]2[CH:6]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[O:8][C:4]=2[CH:3]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 12082972Methyl 6-hydroxy-1-benzofuran-2-carboxylate

Product 1

HCID 12082973Methyl 6-(phenylmethoxy)-2-benzofurancarboxylate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 6-hydroxybenzofuran-2-carboxylate (3.58 g) in THF (30 ml) was slowly added to a suspension of NaH (800 mg) in THF (100 ml) at room temperature, and after stirring for one hour, DMF (35 ml) was added, benzyl bromide (3.77 g) was slowly added and the mixture was stirred for one hour. Water was added to the reaction solution, extraction was performed with AcOEt, and the organic layer was dried with MgSO4 and then filtered and concentrated. The residue was purified by silica gel column chromatography (n-hexane/AcOEt=10/1) to obtain methyl 6-(benzyloxy)benzofuran-2-carboxylate.

Workup

  1. stirringthe mixture was stirred for one hour
  2. dry with materialthe organic layer was dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (n-hexane/AcOEt=10/1)

Sources & evidence

ORD record
ord-43db0f32213e42acbdbd5bbeb0cd62d7
Source dataset
uspto-grants-2003_07
Patent number
US06589984B1

Reaction notes

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