Hydrochloric Acid → HCID 21848328, compound

HRID 618712Notes

Reaction equation

HRID 618712 reaction equation
Br[CH2:2][C:3]1[C:11]2[O:10][C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.[CH2:17]([O-:19])[CH3:18].[Na+].[Na].Cl>C(O)C>[CH2:17]([O:19][CH2:2][C:3]1[C:11]2[O:10][C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1)[CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 22241563HCID 22241563, compound

Product 1

HCID 21848328HCID 21848328, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

4.67 g (16.5 mmol) of ethyl 7-bromomethyl-benzofuran-2-carboxylate were added to a solution of sodium ethanolate in anhydrous ethanol (freshly prepared from 400 mg (17.4 mmol) of sodium in 40 ml of anhydrous ethanol) and the mixture was heated at reflux for one hour. After cooling to room temperature the mixture was poured into 100 ml of 1N HCl and extracted twice with 150 ml of dichloromethane. After drying over magnesium sulfate concentration was carried out in a vacuum. The crude product obtained was purified by column chromatography on silica gel (dichloromethane). There were obtained 2.8 g (69%) of ethyl 7-ethoxymethyl-benzofuran-2-carboxylate as a pale yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for one hour
  3. extractionextracted twice with 150 ml of dichloromethane
  4. dry with materialAfter drying over magnesium sulfate concentration
  5. customThe crude product obtained
  6. customwas purified by column chromatography on silica gel (dichloromethane)

Sources & evidence

ORD record
ord-460304493e3e4429913f74cd0d7eb09c
Source dataset
uspto-grants-1999_09
Patent number
US05955495

Reaction notes

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