Propionic Acid → HCID 178458831, compound

HRID 1780618Notes

Reaction equation

HRID 1780618 reaction equation
[CH3:1][C:2]1([CH3:22])[CH2:6][C:5]2[C:7]([CH3:21])=[C:8]([CH3:20])[C:9]([CH:12]3[CH2:17][C:16](=[O:18])[CH:15]=[C:14]([OH:19])[CH2:13]3)=[C:10]([CH3:11])[C:4]=2[O:3]1.[C:23](O)(=[O:26])[CH2:24][CH3:25].CN(C1C=CC=CN=1)C>C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:22])[CH2:6][C:5]2[C:7]([CH3:21])=[C:8]([CH3:20])[C:9]([CH:12]3[CH2:17][C:16](=[O:18])[C:15]([C:23](=[O:26])[CH2:24][CH3:25])=[C:14]([OH:19])[CH2:13]3)=[C:10]([CH3:11])[C:4]=2[O:3]1

Participants

5

Reactant 3

HCID 1032Propionic AcidHCID 218852-DimethylaminopyridineHCID 19047063HCID 19047063, compound

Product 1

HCID 178458831HCID 178458831, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of 12 g of the 5-(2,3-dihydro-2,2,4,5,7-pentamethylbenzofuran-6-yl)-3-hydroxycyclohex-2-en-1-one in 100 ml of absolute toluene was added 20.5 ml of anhydrous propionic acid and refluxed for 4 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure to afford a residue. To a solution of the residue in 100 ml of absolute toluene was added 0.98 g of dimethylaminopyridine, After refluxing 20 hours, the reaction mixture was cooled to room temperature and concentrated under reduced pressure to afford a crude product. Final purification was carried by silica-gel column chromatography to afford 3.9 g of 5-(2,3-dihydro-2,2,4,5,7-pentamethylbenzofuran-6-yl)-2-propionyl-3-hydroxycyclohex-2-en-1-one as a yellow solid.

Workup

  1. temperaturerefluxed for 4 hours
  2. concentrationconcentrated under reduced pressure
  3. customto afford a residue
  4. temperatureAfter refluxing 20 hours
  5. temperaturethe reaction mixture was cooled to room temperature
  6. concentrationconcentrated under reduced pressure
  7. customto afford a crude product
  8. customFinal purification

Sources & evidence

ORD record
ord-3dbcfaff779d43a7a592e30780f40cb3
Source dataset
uspto-grants-1997_05
Patent number
US05631208

Reaction notes

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