Ethyl 2-(2-formyl-4-methoxyphenoxy)acetate → 2-Benzofurancarboxylic acid, 5-methoxy-, ethyl ester
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
Product 1
Reagents, catalysts & solvents 1
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.