Butyric Acid → HCID 178450315, compound

HRID 1780611Notes

Reaction equation

HRID 1780611 reaction equation
C[C:2]1([CH3:22])[CH2:6][C:5]2[C:7]([CH3:21])=[C:8]([CH3:20])[C:9]([CH3:19])=[C:10]([CH:11]3[CH2:16][C:15](=[O:17])[CH2:14][C:13](=[O:18])[CH2:12]3)[C:4]=2[O:3]1.[C:23]([OH:28])(=O)[CH2:24][CH2:25][CH3:26].[CH3:29]N(C1C=CC=CN=1)C>C1(C)C=CC=CC=1>[C:23]([C:14]1[C:13](=[O:18])[CH2:12][CH:11]([C:10]2[C:4]3[O:3][CH:2]([CH3:22])[CH:6]([CH3:29])[C:5]=3[C:7]([CH3:21])=[C:8]([CH3:20])[C:9]=2[CH3:19])[CH2:16][C:15]=1[OH:17])(=[O:28])[CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 264Butyric AcidHCID 218852-DimethylaminopyridineHCID 190470655-(2,3-Dihydro-2,2,4,5,6-pentamethylbenzofuran-7-yl)cyclohexane-1,3-dione

Product 1

HCID 178450315HCID 178450315, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of 8.3 g of the 5-(2,3-dihydro-2,2,4,5,6-pentamethylbenzofuran-7-yl)cyclohexane-1,3-dione in 80 ml of absolute toluene was added 18 ml of anhydrous butyric acid and refluxed for 4 hours. The reaction mixture was concentrated under reduced pressure to afford a residue. To the solution of the residue in 100 ml of toluene was added 1.6 g of dimethylaminopyridine. After refluxing for 15 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 6.1 g of 2-butyryl-5-(2,3-dihydro-2,3,4,5,6-penta-methylbenzofuran-7-yl)-3-hydroxycyclohex-2-en-1-one as a yellow solid.

Workup

  1. temperaturerefluxed for 4 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customto afford a residue
  4. temperatureAfter refluxing for 15 hours
  5. concentrationconcentrated under reduced pressure
  6. customto afford a crude product
  7. customFinal purification

Sources & evidence

ORD record
ord-c2a60dca5ebe4c6bb4da7e63467a0c56
Source dataset
uspto-grants-1997_05
Patent number
US05631208

Reaction notes

Loading…