Propionic Acid → HCID 178458830, compound

HRID 1780606Notes

Reaction equation

HRID 1780606 reaction equation
[Cl:1][C:2]1[C:10]2[O:9][C:8]([CH3:12])(C)[CH2:7][C:6]=2[C:5]([CH3:13])=[C:4]([CH3:14])[C:3]=1[CH:15]1[CH2:20][C:19](=[O:21])[CH:18]=[C:17]([OH:22])[CH2:16]1.[C:23]([OH:27])(=O)[CH2:24][CH3:25].[C:28]1(C)C=CC=CC=1>CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[C:10]2[O:9][CH:8]([CH3:12])[CH:7]([CH3:28])[C:6]=2[C:5]([CH3:13])=[C:4]([CH3:14])[C:3]=1[CH:15]1[CH2:20][C:19](=[O:21])[C:18]([C:23](=[O:27])[CH2:24][CH3:25])=[C:17]([OH:22])[CH2:16]1

Participants

5

Reactant 3

HCID 1032Propionic AcidHCID 1140Toluene2×HCID 19047067HCID 19047067, compound

Product 1

HCID 178458830HCID 178458830, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

To a solution of 5.9 g of the 5-(7-chloro-2,3-dihydro-2,2,4,5-tetramethyl-benzofuran-6-yl)-3-hydroxycyclohex-2-en-1-one in 70 ml of absolute toluene was added 9.5 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 an oily residue. To the solution of residue in 70 ml of absolute toluene was added 0.67 g of 4-dimethylaminopyridine, refluxed for 15 hours and cooled to room temperature and then concentrated under reduced pressure to afford a crude product. Final purification was carried by silica-gel column chromatography to afford 3.25 g of 5-(7-chloro-2,3-dihydro-2,3,4,5-tetramethylbenzofuran-6-yl)-2-propionyl-3-hydroxycy-clohex-2-en-1-one as a yellow solid.

Workup

  1. temperaturerefluxed for 4 hours
  2. concentrationconcentrated under reduced pressure
  3. customto afford an oily residue
  4. temperaturerefluxed for 15 hours
  5. temperaturecooled to room temperature
  6. concentrationconcentrated under reduced pressure
  7. customto afford a crude product
  8. customFinal purification

Sources & evidence

ORD record
ord-0648df63e17242ae8f6bd9cb9a5d3cc2
Source dataset
uspto-grants-1997_05
Patent number
US05631208

Reaction notes

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