Dimethylformamide → 4-Methoxydibenzofuran

HRID 2039655Notes

Reaction equation

HRID 2039655 reaction equation
[OH:1][C:2]1[C:7]2[O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:15]N(C=O)C.CI>O>[CH3:15][O:1][C:2]1[C:7]2[O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 30150514-Dibenzofuranol

Product 1

HCID 119941974-MethoxydibenzofuranYield 66%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4-hydroxydibenzo[b,d]furan (2 g, 0.0109 mol) in DMF (5 mL) potassium carbonate (3.2 g, 0.0232 mol) and methyl iodide (1.35 mL, 0.0217 mol) was added. The reaction slurry was stirred at room temperature for 3 h. Subsequently the reaction mixture was poured into the cold water (100 mL) and extracted with hexane (3×100 mL). The organic layer was dried over anhydrous sodium sulphate and filtered. The filtrate was evaporated at reduced pressure to, give the desired product in 66% yield, Rf 0.74 (Ethyl acetate:Hexane (3:7); MS m/z: 199.1 (M+1).

Workup

  1. extractionextracted with hexane (3×100 mL)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  3. filtrationfiltered
  4. customThe filtrate was evaporated at reduced pressure to,

Sources & evidence

ORD record
ord-2272469f10144e4b83b743fab68c0100
Source dataset
uspto-grants-2013_11
Patent number
US08580795B2

Reaction notes

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