Cesium carbonate → 5-(4-Methoxy-3-(2-oxo-2-((2-oxotetrahydrofuran-3-yl)oxy)ethyl)phenyl)-dibenzothiophenium iodide

HRID 625186Notes

Reaction equation

[I-:1].[C:2]([CH2:5][C:6]1[CH:7]=[C:8]([S+:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[C:16]3[CH:23]=[CH:24][CH:25]=[CH:26][C:15]2=3)[CH:9]=[CH:10][C:11]=1[O:12][CH3:13])([OH:4])=[O:3].Br[CH:28]1[CH2:32][CH2:31][O:30][C:29]1=[O:33].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[I-:1].[CH3:13][O:12][C:11]1[CH:10]=[CH:9][C:8]([S+:14]2[C:15]3[CH:26]=[CH:25][CH:24]=[CH:23][C:16]=3[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]2=3)=[CH:7][C:6]=1[CH2:5][C:2](=[O:4])[O:3][CH:28]1[CH2:32][CH2:31][O:30][C:29]1=[O:33]

Participants

Conditions

Temperature: 25 °C

Procedure

5-(3-(carboxymethyl)-4-methoxyphenyl)-dibenzothiophenium iodide (50 g, 105 mmol), 3-bromodihydrofuran-2(3H)-one (17.3 g, 105 mmol), and cesium carbonate (68.3 g, 210 mmol) are dissolved in DMF (400 mL) and stirred at 25° C. for 4 h. The reaction mixture is quenched with water (1 L), extracted with DCM (2×400 mL), the combined organic layers washed with water (4×500 mL), concentrated to a viscous oil and precipitated from MTBE (2 L) to afford the title compound as a white solid.

Workup

customThe reaction mixture is quenched with water (1 L)
extractionextracted with DCM (2×400 mL)
washthe combined organic layers washed with water (4×500 mL)
concentrationconcentrated to a viscous oil
customprecipitated from MTBE (2 L)

Sources & evidence

ORD record: ord-059c6fb29353494f8c832326b2bae1e0
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09304394B2

Reaction notes

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