Ethyl 3-methyl-4-methoxy-7-benzoylbenzofuran-2-carboxylate → HCID 15124008, compound

HRID 1084862Notes

Reaction equation

HRID 1084862 reaction equation
[CH3:1][C:2]1[C:6]2[C:7]([O:19]C)=[CH:8][CH:9]=[C:10]([C:11](=[O:18])[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:5]=2[O:4][C:3]=1C(OCC)=O>Cl>[CH3:1][C:2]1[C:6]2[C:7]([OH:19])=[CH:8][CH:9]=[C:10]([C:11](=[O:18])[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:5]=2[O:4][CH:3]=1

Participants

3

Reactant 1

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

Product 1

HCID 15124008HCID 15124008, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
195 °C

Procedure

A mixture of ethyl 3-methyl-4-methoxy-7-benzoylbenzofuran-2-carboxylate (1.10 g, 3.25 mmol) and freshly fused pyridinium hydrochloride (2.14 g, 18.52 mmol) was heated to 195° C. for 45 minutes. After cooling, the reaction mixture was diluted with 2N HCl (25 mL) and extracted with ethyl acetate (3×25 mL). The combined extracts were washed with water (2×20 mL), dried (Na2SO4), and concentrated. Flash chromatography, using 20% ethyl acetate in hexane as eluant, afforded 3-methyl-4-hydroxy-7-benzoylbenzofuran 6. 1H NMR d 2.44 (3H, s), 6.06 (1H, br s), 6.65 (1H, d, J=8 Hz), 7.36 (1H, s), 7.54 (4H, m), 7.84 (2H, m).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate (3×25 mL)
  3. washThe combined extracts were washed with water (2×20 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e78bf59015c4486b90307f1743f57181
Source dataset
uspto-grants-1991_04
Patent number
US05006549

Reaction notes

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