Hydrochloric Acid → HCID 68707325, compound

HRID 2376401Notes

Reaction equation

HRID 2376401 reaction equation
[C:1]([C:4]1[C:12]2[O:11][CH2:10][CH:9]([C:13]3[CH:18]=[CH:17][C:16]([CH:19]([CH3:21])[CH3:20])=[CH:15][CH:14]=3)[C:8]=2[C:7]([CH3:22])=[C:6]([NH:23]C=O)[C:5]=1[CH3:26])(=[O:3])[CH3:2].Cl.C(=O)(O)[O-].[Na+]>CO>[C:1]([C:4]1[C:12]2[O:11][CH2:10][CH:9]([C:13]3[CH:18]=[CH:17][C:16]([CH:19]([CH3:21])[CH3:20])=[CH:15][CH:14]=3)[C:8]=2[C:7]([CH3:22])=[C:6]([NH2:23])[C:5]=1[CH3:26])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 23114040HCID 23114040, compound

Product 1

HCID 68707325HCID 68707325, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-(7-Acetyl-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)formamide obtained in Example 203 (808 mg, 2.3 mmol) was added to a solution of methanol (10 mL) and concentrated hydrochloric acid (5 mL), and the mixture was heated under reflux for 2 hours. The reaction solution was cooled to room temperature and was poured into a cold sodium bicarbonate solution, which was extracted with ethyl acetate. The extract was washed with a saturated brine, dried over sodium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane ethyl acetate=1:1) to obtain the title compound as an oily matter.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. extractionwas extracted with ethyl acetate
  4. washThe extract was washed with a saturated brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane ethyl acetate=1:1)

Sources & evidence

ORD record
ord-5892f54e5b3949d6b78e0bff5e70542f
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

Loading…