Ethyl 2-(2-formyl-4-methoxyphenoxy)acetate → 2-Benzofurancarboxylic acid, 5-methoxy-, ethyl ester

HRID 493167

Reaction equation

HRID 493167 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:8]=1[CH:15]=O)[CH3:2].CC([O-])(C)C.[K+]>C(COC)OC>[CH2:1]([O:3][C:4]([C:5]1[O:6][C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:8]=2[CH:15]=1)=[O:17])[CH3:2]

Participants

4

Reactant 2

HCID 288667Ethyl 2-(2-formyl-4-methoxyphenoxy)acetateHCID 23665647Potassium tert-butoxide

Product 1

HCID 5212832-Benzofurancarboxylic acid, 5-methoxy-, ethyl esterYield 25.5%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

The above prepared (2-formyl-4-methoxy-phenoxy)-acetic acid ethyl ester (34.36 g, 144 mmol) was dissolved in 340 mL of dimethoxyethane and treated at −15° C. with KOtBu (6.47 g, 0.4 eq.). After 15 Min., the reaction mixture was poured onto crashed ice/NH4Cl, twofold extracted with AcOEt, washed with water and brine, dried over magnesium sulfate, and evaporated to dryness. Flash chromatography (SiO2, hexane/AcOEt=9/1) gave finally 8.10 g of the title compound as white crystals.

Workup

  1. addition, the reaction mixture was poured
  2. extractiontwofold extracted with AcOEt
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-5d7f2eae26fb4c82be0fb3ec461ee01e
Source dataset
uspto-grants-2009_05
Patent number
US07534788B2

Linked notes

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