Potassium Carbonate → HCID 86641472, compound

HRID 1893140Notes

Reaction equation

HRID 1893140 reaction equation
F[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[K+].[K+].[C:16]1([SH:32])[C:29]2[C:30]3=[C:31]4[C:26](=[CH:27][CH:28]=2)[CH:25]=[CH:24][CH:23]=[C:22]4[CH:21]=[CH:20][C:19]3=[CH:18][CH:17]=1>CN(C=O)C>[CH:18]1[C:19]2[C:30]3=[C:31]4[C:22](=[CH:21][CH:20]=2)[CH:23]=[CH:24][CH:25]=[C:26]4[CH:27]=[CH:28][C:29]3=[C:16]([S:32][C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[CH:4]=[O:5])[CH:17]=1

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 67970o-FluorobenzaldehydeHCID 22996818HCID 22996818, compound

Product 1

HCID 86641472HCID 86641472, compoundYield 46.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

2-fluoro-benzaldehyde (477 mg, 3.8 mmol), potassium carbonate (700 mg, 5.0 mmol) and pyrene-1-thiol (300 mg, 1.28 mmol) were dissolved in 15 mL of dry DMF under dry nitrogen, topped with a reflux condenser. The reaction mixture was heated to 130° C. for 24 h. After cooling the mixture was added to 50 mL of saturated potassium carbonate solution, and the mixture was extracted with 3 portions of ether. The extracts were dried with magnesium sulfate and evaporated. The residue of the crude product was further purified by chromatography on silica gel using 10:1 petroleum ether (60-80) and EtOAc as eluent to afford a yellow solid (200 mg, 46%). 1H-NMR (500 MHz, CDCl3): δ 6.56 (dd, J=0.8, 7.9 Hz, 1H), 7.07-7.22 (m, 2H), 7.89 (dd, J=1.7, 7.2 Hz, 1H), 8.02-8.28 (m, 8H), 8.58 (d, J=9.2 Hz, 1H), 10.45 (s, 1H). 13C-NMR (125 MHz, CDCl3): δ 124.7, 124.9, 125.3, 125.5, 125.9, 126.0, 126.4, 127.1, 128.0, 128.7, 129.0, 130.8, 131.0, 132.5, 133.3, 133.4, 133.8, 133.9, 137.0, 143.2, 191.6. EI-MS: m/z M+Calculated 338.1, found 338.1.

Workup

  1. customtopped with a reflux condenser
  2. temperatureAfter cooling the mixture
  3. extractionthe mixture was extracted with 3 portions of ether
  4. dry with materialThe extracts were dried with magnesium sulfate
  5. customevaporated
  6. customThe residue of the crude product was further purified by chromatography on silica gel using 10:1 petroleum ether (60-80) and EtOAc as eluent

Sources & evidence

ORD record
ord-ed670910f1164d199cdc2813ce03105f
Source dataset
uspto-grants-2013_08
Patent number
US08513151B2

Reaction notes

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