Potassium Carbonate → 5-[(4-Methoxyphenyl)thio]-2-furancarboxaldehyde

HRID 382447Notes

Reaction equation

HRID 382447 reaction equation
Br[C:2]1[O:3][C:4]([CH:7]=[O:8])=[CH:5][CH:6]=1.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([SH:17])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([S:17][C:2]2[O:3][C:4]([CH:7]=[O:8])=[CH:5][CH:6]=2)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 127654-MethoxybenzenethiolHCID 6003285-Bromofuran-2-carbaldehyde

Product 1

HCID 122305495-[(4-Methoxyphenyl)thio]-2-furancarboxaldehydeYield 91.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-bromo-5-furaldehyde (20.0 g, 114.29 mmol) in acetone (200 mL) was added 4-methoxybenzenethiol (15.5 mL, 125.75 mmol) and potassium carbonate (20 g). The reaction mixture was stirred at room temperature for 19 hours, and then filtered and concentrated on a rotary evaporator. The solid obtained was recrystallized from hexanes (300 mL) and ethyl acetate (50 mL) to give yellowish crystals (24.50 g).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated on a rotary evaporator
  3. customThe solid obtained
  4. customwas recrystallized from hexanes (300 mL) and ethyl acetate (50 mL)

Sources & evidence

ORD record
ord-0e1ecd518271403ba531788b7377177c
Source dataset
uspto-grants-2001_10
Patent number
US06310092B1

Reaction notes

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