Carbon Dioxide → HCID 10855983, compound

HRID 1107519Notes

Reaction equation

HRID 1107519 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[C:11](Br)=[CH:10][CH:9]=[CH:8][C:5]=2[C:6]=1[CH3:7].[C:13](=O)=[O:14].C([Li])(C)(C)C.CN(C)C=O>CC(C)=O.O.O1CCCC1>[CH3:1][C:2]1[O:3][C:4]2[C:11]([CH:13]=[O:14])=[CH:10][CH:9]=[CH:8][C:5]=2[C:6]=1[CH3:7]

Participants

8

Reactant 4

HCID 280Carbon DioxideHCID 6228DimethylformamideHCID 110962627-BROMO-2,3-DIMETHYL-1-BENZOFURANHCID 178418306HCID 178418306, compound

Product 1

HCID 10855983HCID 10855983, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

17 g (75.6 mmol) of 2,3-dimethyl-7-bromobenzofuran and 250 ml of tetrahydrofuran are introduced under an inert atmosphere into a 1 liter round-bottomed flask. The mixture is cooled to -78° C. by a bath of dry ice in acetone. 60 ml of tert-butyllithium (1.4M in pentane) are added dropwise and the reaction mixture is allowed to stir for 10 minutes. 17.5 ml of N,N-dimethylformamide (227 mmol) are then added dropwise and the reaction mixture is allowed to return to room temperature. 100 ml of water are added and then extraction is carried out with ethyl acetate (3×80 ml). The organic phases are combined, dried over magnesium sulphate and concentrated. The residue is purified by chromatography on a silica column (elution solvent cyclohexane: ethyl acetate 9:1). 11.97 g (Yield: 91%) of 2,3-dimethyl-7-formylbenzofuran are obtained. M.p. =56-58° C.

Workup

  1. customto return to room temperature
  2. extractionextraction
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated
  5. customThe residue is purified by chromatography on a silica column (elution solvent cyclohexane: ethyl acetate 9:1)

Sources & evidence

ORD record
ord-496263d3559a494496899d5da4c7f2e3
Source dataset
uspto-grants-2000_05
Patent number
US06060508

Reaction notes

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