Tetrahydrofuran → HCID 23035562, compound

HRID 1710151Notes

Reaction equation

HRID 1710151 reaction equation
C([Li])CCC.O1CCCC1.Br[C:12]1[CH:13]=[C:14]([O:20][CH3:21])[C:15]([O:18][CH3:19])=[CH:16][CH:17]=1.[S:22]1[CH:26]=[CH:25][C:24]([CH:27]=[O:28])=[CH:23]1>CCCCCC.O>[OH:28][CH:27]([C:24]1[CH:25]=[CH:26][S:22][CH:23]=1)[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 681353-ThiophenecarboxaldehydeHCID 76114Benzene, 4-bromo-1,2-dimethoxy-HCID 178418339Butyllithium

Product 1

HCID 23035562HCID 23035562, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

24 ml of 2.5M n-butyl lithium in hexane are added dropwise to a tetrahydrofuran solution of 10.85 g 4-bromoveratrole under cooling. After stirring the mixture, 5.61 g of 3-thiophenecarboaldehyde are added thereto, and warmed to room temperature. Water is added thereto, and the mixture is extracted with ethyl acetate. The extract is dried and evaporated under reduced pressure to remove the solvent, whereby 3-(α-hydroxy-3,4-dimethoxybenzyl)thiophene is obtained. 2.8 g of sodium hydride are added to a solution of the product in dimethylformamide, and the mixture is stirred at room temperature. 4.7 ml of methyl iodide are added thereto, and the mixture is stirred. A small amount of water is added thereto, and the mixture is evaporated under reduced pressure to remove the solvent. Water is added to the residue and the mixture is extracted with ethyl acetate. The extract is dried and evaporated under reduced pressure to remove the solvent. The residue is purified by using silica gel column, whereby 10.5 g of 3-(α-methoxy-3,4-dimethoxybenzyl)thiophene are obtained.

Workup

  1. temperatureunder cooling
  2. additionare added
  3. extractionthe mixture is extracted with ethyl acetate
  4. customThe extract is dried
  5. customevaporated under reduced pressure
  6. customto remove the solvent

Sources & evidence

ORD record
ord-07b3e088c12444039ded9cb39b04cfc7
Source dataset
uspto-grants-1990_08
Patent number
US04952602

Reaction notes

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