Potassium Carbonate → HCID 86640045, compound

HRID 452783Notes

Reaction equation

[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]3[O:14][CH:13]=[C:12]([C:15]4[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=4)[C:11]=3[CH:22]=2)=[N:4][N:3]=1.[CH3:23][S:24](Cl)(=[O:26])=[O:25].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[CH3:23][S:24]([O:21][C:18]1[CH:17]=[CH:16][C:15]([C:12]2[C:11]3[CH:22]=[C:7]([C:5]4[O:6][C:2]([CH3:1])=[N:3][N:4]=4)[CH:8]=[CH:9][C:10]=3[O:14][CH:13]=2)=[CH:20][CH:19]=1)(=[O:26])=[O:25]

Participants

Conditions

Temperature: 60 °C

Procedure

A suspension of 4-[5-(5-methyl-1,3,4-oxadiazol-2-yl)-1-benzofuran-3-yl]phenol (351 mg, 1.20 mmol), methanesulfonyl chloride (0.111 mL, 1.44 mmol) and potassium carbonate (332 mg, 2.40 mmol) in N,N-dimethylformamide (5 mL) was stirred at room temperature for 2 hr and at 60° C. overnight. The reaction mixture was diluted with ethyl acetate. The mixture was washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=10/1-1/1) and recrystallized from hexane/ethyl acetate to give the title compound (107 mg, yield 24%) as colorless crystals.

Workup

washThe mixture was washed with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=10/1-1/1)
customrecrystallized from hexane/ethyl acetate

Sources & evidence

ORD record: ord-761e9b3396344ab584299e00f0840c41
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492378B2

Reaction notes

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