HCID 19748779, compound → HCID 19748798, compound

HRID 484052Notes

Reaction equation

HRID 484052 reaction equation
C(O[CH:4](OCC)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:9][CH:8]=1)C>C1C=CC=CC=1>[O:6]1[C:7]2[CH:12]=[CH:11][C:10]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:9][C:8]=2[CH:4]=[CH:5]1

Participants

3

Reactant 1

HCID 19748779HCID 19748779, compound

Product 1

HCID 19748798HCID 19748798, compoundYield 29.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

In a 1 L 3-necked flask equipped with a mechanical stirrer and a condenser was added polyphosphoric acid (80 gm) and benzene (450 mL). This mixture was heated to reflux for 15 min and then ethyl 4-[(2,2-diethoxy)ethoxy]phenylacetate (86 gm, 0.29 mol) in benzene (50 mL) was added and the reflux was continued for 40 min. The reaction mixture was cooled and the mobile phase was decanted off. This benzene solution was washed successively with H2O, sat. NaHCO3, and sat. NaCl before being dried over Na2SO4, filtered and evaporated to dryness. This residue was dissolved in 10-15% EtOAc in hexane and passed through a short silica gel column (5 cm×10 cm dia.) in the same solvent. The eluent was evaporated to dryness to give a yellow liquid which was further purified by preparative LC using 10% EtOAc in hexane as eluent to give 17.4 gm of ethyl benzofuran-5-ylacetate.

Workup

  1. customIn a 1 L 3-necked flask equipped with a mechanical stirrer and a condenser
  2. temperatureThis mixture was heated
  3. temperatureto reflux for 15 min
  4. temperatureThe reaction mixture was cooled
  5. customthe mobile phase was decanted off
  6. washThis benzene solution was washed successively with H2O, sat. NaHCO3, and sat. NaCl
  7. dry with materialbefore being dried over Na2SO4
  8. filtrationfiltered
  9. customevaporated to dryness
  10. dissolutionThis residue was dissolved in 10-15% EtOAc in hexane
  11. customThe eluent was evaporated to dryness
  12. customto give a yellow liquid which
  13. customwas further purified by preparative LC

Sources & evidence

ORD record
ord-f9ab9afae9fd481a8446f85cdedabd59
Source dataset
uspto-grants-1993_07
Patent number
US05229381

Reaction notes

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