Diethyl Ether → 2-Benzofurancarboxaldehyde, 5-methyl-

HRID 2243175Notes

Reaction equation

HRID 2243175 reaction equation
C[O:2][CH:3](OC)[CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][C:7]=1[CH:8]=O.CCOCC>FC(F)(F)C(O)=O>[CH3:14][C:11]1[CH:12]=[CH:13][C:6]2[O:5][C:4]([CH:3]=[O:2])=[CH:8][C:7]=2[CH:10]=1

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 86614071HCID 86614071, compound

Product 1

HCID 106785342-Benzofurancarboxaldehyde, 5-methyl-Yield 68.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

154 mg (0.69 mmol) of 2-(2,2-dimethoxy-ethoxy)-5-methyl-benzaldehyde were dissolved in trifluoroacetic acid and the reaction mixture was heated to reflux for 15 min. After cooling to RT ether was added and the mixture was washed with water and 10% aqueous KHCO3 solution. The organic layer was then dried (MgSO4) and concentrated and the residue was purified by column chromatography (silica gel; ethyl acetate/cyclohexane 4:1) to yield 76 mg (48%) of 5-methyl-benzofuran-2-carbaldehyde as brown oil. 1HNMR (CDCl3, 300 MHz): δ 2.47 (s, 3H), 7.34 (d, J=8.7 Hz, 1H), 7.50 (m, 3H), 9.85 (s, 1H).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 15 min
  3. additionwas added
  4. washthe mixture was washed with water and 10% aqueous KHCO3 solution
  5. dry with materialThe organic layer was then dried (MgSO4)
  6. concentrationconcentrated
  7. customthe residue was purified by column chromatography (silica gel; ethyl acetate/cyclohexane 4:1)

Sources & evidence

ORD record
ord-85bbb2285ab140a498f0814691a80d66
Source dataset
uspto-grants-2010_03
Patent number
US07674815B2

Reaction notes

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