Hydrochloric Acid → Ethyl 7-methoxy-1-benzofuran-2-carboxylate

HRID 636530Notes

Reaction equation

HRID 636530 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][O:7][C:8]1[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[CH:12][C:9]=1[CH:10]=O)=[O:5])[CH3:2].CC(C)([O-])C.[K+].O.Cl>O1CCCC1>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[CH:12][C:9]=2[CH:10]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 2229635Ethyl 2-(2-formyl-6-methoxyphenoxy)acetateHCID 23665647Potassium tert-butoxide

Product 1

HCID 521284Ethyl 7-methoxy-1-benzofuran-2-carboxylateYield 19.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-ethoxycarbonylmethoxy-3-methoxybenzaldehyde (2.00 g) and potassium tert-butoxide (96 mg) in tetrahydrofuran (20 ml) was stirred for 1 hour under ice-cooling. Water was added to the reaction mixture, and the solution was neutralized with 1N hydrochloric acid and extracted with ethyl acetate. The extract was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin layer chromatography (n-hexane:ethyl acetate=7:1, v/v) to give 2-ethoxycarbonyl-7-methoxybenzofuran (360 mg).

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by preparative thin layer chromatography (n-hexane

Sources & evidence

ORD record
ord-3ee6b20ab77d4a4f953889d5cb4149aa
Source dataset
uspto-grants-2001_02
Patent number
US06194396B1

Reaction notes

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