Hydrochloric Acid → Ethyl 3-methyl-4-methoxy-7-benzoylbenzofuran-2-carboxylate

HRID 1084861Notes

Reaction equation

HRID 1084861 reaction equation
[CH3:1][C:2]1[C:6]2[C:7]([O:11][CH3:12])=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>ClCCCl>[CH3:1][C:2]1[C:6]2[C:7]([O:11][CH3:12])=[CH:8][CH:9]=[C:10]([C:18](=[O:25])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:5]=2[O:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 9497663Ethyl 4-methoxy-3-methyl-2-benzofurancarboxylate

Product 1

HCID 15124007Ethyl 3-methyl-4-methoxy-7-benzoylbenzofuran-2-carboxylate

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of ethyl 3-methyl-4-methoxybenzofuran-2-carboxylate (1.00 g, 4.27 mmol) and benzoyl chloride (1.80 g, 12.81 mmol) in 1,2-dichloroethane (12 mL) was added aluminum chloride (1.71 g, 12.81 mmol) in portions. The mixture was heated to reflux for 1.5 hours then allowed to cool and poured into 2N HCl (50 mL). The resulting mixture was extracted with methylene chloride (3×30 mL) and the combined extracts washed with saturated NaHCO3 (3×25 mL), dried (Na2SO4), and concentrated. The crude product was purified by preparative HPLC, using 25% ethyl acetate in hexane as eluant, to afford ethyl 3-methyl-4-methoxy-7-benzoylbenzofuran-2-carboxylate mp. 137°-139° C.; 1H NMR d 1.27 (2H, t, J=6 Hz), 2.67 (3H, s), 3.95 (3H, s), 4.28 (2H, q, J=6 Hz), 6.66 (1H, d, J=8 Hz), 7.44 (3H, m), 7.72 (3H, m).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1.5 hours
  3. temperatureto cool
  4. extractionThe resulting mixture was extracted with methylene chloride (3×30 mL)
  5. washthe combined extracts washed with saturated NaHCO3 (3×25 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-4f739b9da9064a2c999752a0d28c0d85
Source dataset
uspto-grants-1991_04
Patent number
US05006549

Reaction notes

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