HCID 22918668, compound → HCID 22918658, compound

HRID 1452386Notes

Reaction equation

HRID 1452386 reaction equation
[C:1]([O:4][C:5]1[C:6]([C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:7][C:8]2[O:12][C:11]([CH2:14][CH2:15][CH:16]3OCC[O:17]3)([CH3:13])[CH2:10][C:9]=2[C:21]=1[C:22]([CH3:25])([CH3:24])[CH3:23])(=[O:3])[CH3:2]>C(O)(=O)C>[C:1]([O:4][C:5]1[C:6]([C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:7][C:8]2[O:12][C:11]([CH2:14][CH2:15][CH:16]=[O:17])([CH3:13])[CH2:10][C:9]=2[C:21]=1[C:22]([CH3:25])([CH3:24])[CH3:23])(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 22918668HCID 22918668, compound

Product 1

HCID 22918658HCID 22918658, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5-Acetoxy-2-[2-(1,3-dioxa-2-cyclopentyl)ethyl]-4,6-di-tert-butyl-2-methyl-2,3-dihydrobenzofuran (17.3 g) was dissolved in 80% acetic acid (150 ml) and the solution was heated under reflux for 1 h. After cooling the solution, the acetic acid was distilled off under vacuum and, after addition of water, the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, then dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by silica gel chromatography (25% ethyl acetate in n-hexane) to afford 5-acetoxy-4,6-di-tert-butyl-2-(2-formylethyl)-2-methyl-2,3-dihydrobenzofuran quantitatively (15.53 g) as a colorless oil.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 1 h
  3. temperatureAfter cooling the solution
  4. distillationthe acetic acid was distilled off under vacuum
  5. additionafter addition of water
  6. extractionthe resulting mixture was extracted with ethyl acetate
  7. washThe organic layer was washed with water and saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated
  10. customThe concentrate was purified by silica gel chromatography (25% ethyl acetate in n-hexane)

Sources & evidence

ORD record
ord-5680c654e8154e319b0ec333af18ded0
Source dataset
uspto-grants-1997_02
Patent number
US05606089

Reaction notes

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