Ethyl Acetate → HCID 18673882, compound

HRID 1635977Notes

Reaction equation

HRID 1635977 reaction equation
Cl[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][N:3]=1.[OH:13][C:14]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:15]=1[CH2:16][CH2:17][C:18]2=[O:23].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C=O)C.O>[O:23]=[C:18]1[C:19]2[C:15](=[C:14]([O:13][C:2]3[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][N:3]=3)[CH:22]=[CH:21][CH:20]=2)[CH2:16][CH2:17]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 5905474-Hydroxy-1-indanoneHCID 2799611Ethyl 6-chloronicotinate

Product 1

HCID 18673882HCID 18673882, compoundYield 84.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

1.86 g of ethyl 6-chloronicotinate and 1.48 g of 4-hydroxy-1-indanone were dissolved in 15 ml of DMF. To the resulting solution, 0.97 g of potassium carbonate was added and the mixture was stirred at 120° C. After 1 hour, ethyl acetate and water were added to the reaction solution, thereby partitioning between an organic layer and an aqueous layer. The organic layer was washed with a saturated sodium chloride solution, dried over magnesium sulfate and then concentrated under reduced pressure. The residual oily substance was purified by column chromatography (eluent: ethyl acetate/n-hexane (1:4)) to obtain the titled compound (2.52 g) as an oily substance.

Workup

  1. custompartitioning between an organic layer
  2. washThe organic layer was washed with a saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residual oily substance was purified by column chromatography (eluent: ethyl acetate/n-hexane (1:4))

Sources & evidence

ORD record
ord-282556b72d32483fae9949e078055239
Source dataset
uspto-grants-2003_01
Patent number
US06511995B1

Reaction notes

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