Potassium Carbonate → 7-(2-Trimethylsilylethylthio)-4-(3-furyl)coumarin

HRID 741832Notes

Reaction equation

HRID 741832 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:13]3[CH:17]=[CH:16][O:15][CH:14]=3)=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1.[CH3:18][Si:19]([CH3:24])([CH3:23])[CH2:20][CH2:21][SH:22].C([O-])([O-])=O.[K+].[K+].[NH4+].[Cl-]>CN1CCCC1=O>[CH3:18][Si:19]([CH3:24])([CH3:23])[CH2:20][CH2:21][S:22][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:13]3[CH:17]=[CH:16][O:15][CH:14]=3)=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 2055212-(Trimethylsilyl)ethanethiolHCID 153824547-Bromo-4-(3-furyl)coumarin

Product 1

HCID 233702447-(2-Trimethylsilylethylthio)-4-(3-furyl)coumarinYield 54.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 7-bromo-4-(furan-3-yl)coumarin (Coumarin 4) (1.5 g, 5.15 mmol), 2-(trimethylsilyl)ethanethiol (830 mg, 6.18 mmol), and K2CO3 (1.77 g, 12.9 mmol) in 1-methyl-2-pyrrolidinone (12 mL) was heated at 105° C. for 4 h. After cooling, them was added saturated aqueous NH4Cl (10 mL), then H2O (50 mL) and the mixture was extracted twice with EtOAc. The organic extracts were washed 4 times with H2O, dried over MgSO4 and evaporated to a residue which was chromatographed on silica gel eluting with a 1:3 mixture of EtOAc and hexane, to afford the title compound (963 mg) as a tan solid.

Workup

  1. temperatureAfter cooling
  2. extractionH2O (50 mL) and the mixture was extracted twice with EtOAc
  3. washThe organic extracts were washed 4 times with H2O
  4. dry with materialdried over MgSO4
  5. customevaporated to a residue which
  6. customwas chromatographed on silica gel eluting with a 1:3 mixture of EtOAc and hexane

Sources & evidence

ORD record
ord-2abd8ba310054afcaf8f94ed05d53dc5
Source dataset
uspto-grants-1996_09
Patent number
US05552437

Reaction notes

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