Pyridine → HCID 178450313, compound

HRID 846003Notes

Reaction equation

HRID 846003 reaction equation
[CH3:1][CH2:2][CH2:3][C:4](Cl)=[O:5].N1C=CC=CC=1.[OH:13][C:14]1[CH2:19][CH:18]([C:20]2[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[CH:22][C:21]=2[CH3:28])[CH2:17][C:16](=[O:29])[CH:15]=1.ClCCl>O>[C:4]([C:15]1[C:14](=[O:13])[CH2:19][CH:18]([C:20]2[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[CH:22][C:21]=2[CH3:28])[CH2:17][C:16]=1[OH:29])(=[O:5])[CH2:3][CH2:2][CH3:1]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 8855Butyryl chlorideHCID 137985663-Hydroxy-5-mesitylcyclohex-2-en-1-one

Product 1

HCID 178450313HCID 178450313, compoundYield 36.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

n-Butyryl chloride (2.3 g; 21.7 mmole) and then pyridine (1.7 g; 21.7 mmole) were added to a stirred mixture of 3-hydroxy-5-mesitylcyclohex-2-en-1-one (5.0 g; 21.7 mmole) and dichloromethane (50 ml) under a nitrogen atmosphere. The mixture was stirred at room temperature for a period of two hours and then poured into slightly acidic water. The organic phase was separated and the aqueous phase was thoroughly extracted with dichloromethane. The combined organic phase and extracts were washed with water, dried over anhydrous magnesium sulfate and the solvent was removed by evaporation under reduced pressure using a rotary evaporator. The residue was dissolved in 1,2-dichloroethane (50 ml), stannic chloride (5.7 g; 22 mmole) was added and the mixture was heated under reflux for a period of 8 hours. The mixture was cooled and poured into water and the aqueous mixture was extracted several times with dichloromethane. The combined organic extracts were dried over anhydrous magnesium sulfate and the solvent was removed by evaporation under reduced pressure using a rotary evaporator. The residue was purified by chromatography over silica gel (eluant dichloromethane) to give 2-butyryl-3-hydroxy-5-mesitylcyclohex-2-en-1-one (2.4 g). Proton nuclear magnetic resonance spectrum (CDCl3 : δ in ppm): 1.01 (3H, t); 1.30-1.60 (2H, m); 2.23 (3H, s); 2.37 (6H, s); 2.40-3.45 (7H, m); 6.83 (2H, s); 18.24 (1H, s).

Workup

  1. customThe organic phase was separated
  2. extractionthe aqueous phase was thoroughly extracted with dichloromethane
  3. washThe combined organic phase and extracts were washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed by evaporation under reduced pressure
  6. customa rotary evaporator
  7. dissolutionThe residue was dissolved in 1,2-dichloroethane (50 ml)
  8. temperaturethe mixture was heated
  9. temperatureunder reflux for a period of 8 hours
  10. temperatureThe mixture was cooled
  11. extractionthe aqueous mixture was extracted several times with dichloromethane
  12. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  13. customthe solvent was removed by evaporation under reduced pressure
  14. customa rotary evaporator
  15. customThe residue was purified by chromatography over silica gel (eluant dichloromethane)

Sources & evidence

ORD record
ord-0b6a4ac4310944349ae399435687a937
Source dataset
uspto-grants-1988_07
Patent number
US04760192

Reaction notes

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