1,2-Dimethoxyethane → 4-Furan-3-yl-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester

HRID 29370

Reaction equation

[C:1]([O:5][C:6]([C:8]1[O:9][C:10]2[CH:17]=[CH:16][CH:15]=[C:14](OS(C(F)(F)F)(=O)=O)[C:11]=2[C:12]=1[CH3:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[O:32]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33]1.COCCOC>O>[C:1]([O:5][C:6]([C:8]1[O:9][C:10]2[CH:17]=[CH:16][CH:15]=[C:14]([C:34]3[CH:35]=[CH:36][O:32][CH:33]=3)[C:11]=2[C:12]=1[CH3:13])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 85 °C

Procedure

3-Methyl-4-trifluoromethanesulfonyloxy-benzofuran-2-carboxylic acid tert-butyl ester (285 mg, 0.75 mmol) was mixed with K2CO3 (207 mg, 2.2 eq), furan-3-boronic acid (101 mg, 1.2 eq), Pd(Ph3)4 (43 mg, 0.05 eq), 3 mL of 1,2-dimethoxyethane and 0.5 mL of water. The mixture was heated and stirred in a 85° C. oil bath for 2 h. The reaction mixture was poured into water and was extracted with ethyl acetate. The organic extract was washed with water and dried over sodium sulfate. Removal of the solvent in vacuo gave the crude product, which was purified by column chromatography to give 153 mg of 4-furan-3-yl-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester, obtained as white solid.

Workup

temperatureThe mixture was heated
extractionwas extracted with ethyl acetate
extractionThe organic extract
washwas washed with water
dry with materialdried over sodium sulfate
customRemoval of the solvent in vacuo
customgave the crude product, which
customwas purified by column chromatography

Sources & evidence

ORD record: ord-192bf958dc894ec9b93651037a8bedf4
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07420001B2

Linked notes

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