Tetrahydrofuran → Methyl 2-(4-nitrophenyl)benzofuran-7-carboxylate

HRID 1761908Notes

Reaction equation

HRID 1761908 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12]3[C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=[CH:15][C:13]=3[CH:14]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].O1CCC[CH2:23]1>>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12]3[C:18]([C:19]([O:21][CH3:23])=[O:20])=[CH:17][CH:16]=[CH:15][C:13]=3[CH:14]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 142297282-(4-Nitrophenyl)benzofuran-7-carboxylic acid

Product 1

HCID 14229713Methyl 2-(4-nitrophenyl)benzofuran-7-carboxylate

Procedure

A diazomethane-ether solution (prepared from 5.0 g of nitrosomethylurea) is added to a solution of 6.0 g of 2-(4-nitrophenyl)benzofuran-7-carboxylic acid in 60 ml of tetrahydrofuran and the mixture is stirred at room temperature for 1 hour. The reaction mixture is evaporated to remove solvent and the residue is dissolved in ethyl acetate. The solution is washed with water, dried and evaporated to remove solvent. The residue is washed with ethyl acetate and dried to give 3.82 g of methyl 2-(4-nitrophenyl)benzofuran-7-carboxylate as pale brown powder.

Workup

  1. customThe reaction mixture is evaporated
  2. customto remove solvent
  3. dissolutionthe residue is dissolved in ethyl acetate
  4. washThe solution is washed with water
  5. customdried
  6. customevaporated
  7. customto remove solvent
  8. washThe residue is washed with ethyl acetate
  9. customdried

Sources & evidence

ORD record
ord-0897e720d4e74ffa9f9a8c4b94f8a771
Source dataset
uspto-grants-1989_05
Patent number
US04829067

Reaction notes

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