Butyric Acid → HCID 178450310, compound

HRID 1780601Notes

Reaction equation

HRID 1780601 reaction equation
[CH3:1][C:2]1([CH3:22])[CH2:6][C:5]2[C:7]([CH3:21])=[C:8]([CH:13]3[CH2:18][C:17](=[O:19])[CH2:16][C:15](=[O:20])[CH2:14]3)[C:9]([CH3:12])=[C:10]([CH3:11])[C:4]=2[O:3]1.[C:23](O)(=[O:27])[CH2:24][CH2:25][CH3:26]>C1(C)C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:23]([C:16]1[C:17](=[O:19])[CH2:18][CH:13]([C:8]2[C:9]([CH3:12])=[C:10]([CH3:11])[C:4]3[O:3][C:2]([CH3:22])([CH3:1])[CH2:6][C:5]=3[C:7]=2[CH3:21])[CH2:14][C:15]=1[OH:20])(=[O:27])[CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 2

HCID 264Butyric AcidHCID 19047076HCID 19047076, compound

Product 1

HCID 178450310HCID 178450310, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent2×

Procedure

To a solution of 3.18 g of the 5-(2,3-dihydro-2,2,4,6,7-pentamethylbenzofuran-5-yl)cyclohexane-1,3-dione in 50 ml of absolute toluene was added 6.93 ml of anhydrous butyric 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 the residue in 50 ml of absolute toluene was added 0.26 g of 4-dimethylaminopyridine. After refluxing 8 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 3.8 g of 2-butyryl-5-(2,3-dihydro-2,2,4,6,7-pentamethylbenzofuran-5-yl)-3-hydroxycyclohex-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. temperatureAfter refluxing 8 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-6bcf4fe6cc0d4d90955232d7d09c9782
Source dataset
uspto-grants-1997_05
Patent number
US05631208

Reaction notes

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