1,2-Dimethoxyethane → 3-Methyl-4-phenyl-benzofuran-2-carboxylic acid tert-butyl ester

HRID 29356Notes

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+].[C:32]1(B(O)O)[CH:37]=[CH:36][CH:35]=[CH:34][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:32]3[CH:37]=[CH:36][CH:35]=[CH:34][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 (85 mg, 0.25 mmol) was mixed with K2CO3 (68 mg, 0.5 mmol), phenylboronic acid (31 mg, 0.25 mmol), Pd(Ph3)4 (14 mg, 0.01 mmol), 1 mL of 1,2-dimethoxyethane and 2 drops of water. The mixture was heated and stirred in an 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. Filtration followed by removal of the solvent in vacuo gave the crude product (71 mg), which was purified by column chromatography to give 53 mg (77% yield) of 3-methyl-4-phenyl-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
filtrationFiltration
customfollowed by removal of the solvent in vacuo
customgave the crude product (71 mg), which
customwas purified by column chromatography

Sources & evidence

ORD record: ord-e097fe578d814ac1a945e082a61e03c5
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07420001B2

Reaction notes

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