Carbon Dioxide → 2,3-Dimethyl-6-methoxybenzofuran

HRID 1107865Notes

Reaction equation

HRID 1107865 reaction equation
[CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][C:9](O)=[CH:10][C:5]=2[O:4][CH:3]=1.[C:12](=[O:14])=O.[CH:15]([N-]C(C)C)(C)C.[Li+].CI>CC(C)=O.O.O1CCCC1>[CH3:15][C:3]1[O:4][C:5]2[CH:10]=[C:9]([O:14][CH3:12])[CH:8]=[CH:7][C:6]=2[C:2]=1[CH3:1]

Participants

8

Reactant 4

HCID 280Carbon DioxideHCID 6328Methyl iodideHCID 2724682Lithium diisopropylamideHCID 108556243-Methyl-6-hydroxybenzofuran

Product 1

HCID 107259582,3-Dimethyl-6-methoxybenzofuran

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.7 g (4.3 mmol) of 3-methyl-6-hydroxybenzofuran and 35 ml of tetrahydrofuran are introduced into a 50 ml three-necked flask. Cooling is carried out to -78° C. with a bath of solid carbon dioxide in acetone. 2.6 ml of lithium diisopropylamide (2.0M in tetrahydrofuran/heptane) are added dropwise and stirring is continued for 20 min. 0.535 ml of methyl iodide is then added dropwise. The reaction mixture is allowed to return to room temperature. 50 ml of water are added and then extraction is carried out with ethyl acetate (3×50 ml). The organic phases are combined, dried over magnesium sulphate and concentrated. The residue is subjected a second time to the same treatment. 0.691 g of 2,3-dimethyl-6-methoxybenzofuran is obtained in the form of an oil.

Workup

  1. temperatureCooling
  2. customto return to room temperature
  3. extractionextraction
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4c976ff109804927b4d3a59d090de808
Source dataset
uspto-grants-2000_05
Patent number
US06063810

Reaction notes

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