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

HRID 2287606

Reaction equation

HRID 2287606 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 (963 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-6485e4f1f2034e4d889cfaa6e2475f4d
Source dataset
uspto-grants-2000_07
Patent number
US06083961

Linked notes

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