HCID 67403812, compound → HCID 67401930, compound

HRID 906089Notes

Reaction equation

HRID 906089 reaction equation
[CH3:1][C:2]1[C:10]2[O:9][CH:8](OC)[CH2:7][C:6]=2[CH:5]=[CH:4][C:3]=1[C:13]([O:15][CH3:16])=[O:14]>P(=O)(O)(O)O>[CH3:1][C:2]1[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[CH:5]=[CH:4][C:3]=1[C:13]([O:15][CH3:16])=[O:14]

Participants

3

Reactant 1

HCID 67403812HCID 67403812, compound

Product 1

HCID 67401930HCID 67401930, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 1004Phosphoric AcidSolvent

Conditions

Temperature
100 °C

Procedure

A solution of methyl 7-methyl-2-(methyloxy)-2,3-dihydro-1-benzofuran-6-carboxylate in phosphoric acid (3 mL) was stirred at room temperature for 10 minutes and then was stirred at 100° C. for 15 minutes. The reaction mixture was cooled to room temperature and then was partitioned between water and diethyl ether. The aqueous portion was extracted three times with diethyl ether. The combined organic portion was washed three times with water and twice with 10% aqueous potassium carbonate. The basic portion was extracted three times with diethyl ether and the combined organic portions were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to afford a brown residue which was purified by column chromatography eluting with 5% ethyl acetate in hexanes. Pure fractions were concentrated in vacuo to afford (371 mg, 54%) of methyl 7-methyl-1-benzofuran-6-carboxylate as a colorless oil.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customwas partitioned between water and diethyl ether
  3. extractionThe aqueous portion was extracted three times with diethyl ether
  4. washThe combined organic portion was washed three times with water
  5. extractionThe basic portion was extracted three times with diethyl ether
  6. washthe combined organic portions were washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto afford a brown residue which
  11. customwas purified by column chromatography
  12. washeluting with 5% ethyl acetate in hexanes
  13. concentrationPure fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-256c70f5b1a74f8699c0a356601c67b8
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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