2-Dimethylaminopyridine → HCID 136200006, compound

HRID 1870640Notes

Reaction equation

HRID 1870640 reaction equation
[Cl:1][C:2]1[C:10]([CH3:11])=[C:9]2[C:5]([CH2:6][C:7]([CH2:13][CH3:14])([CH3:12])[CH2:8]2)=[C:4]([CH3:15])[C:3]=1[CH:16]1[CH2:21][C:20](=[O:22])[CH2:19][C:18](=[O:23])[CH2:17]1.C(O[C:29](=[O:32])[CH2:30]C)(=O)CC.C[N:34]([C:36]1[CH:41]=[CH:40]C=CN=1)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:10]([CH3:11])=[C:9]2[C:5]([CH2:6][C:7]([CH2:13][CH3:14])([CH3:12])[CH2:8]2)=[C:4]([CH3:15])[C:3]=1[CH:16]1[CH2:21][C:20](=[O:22])[C:19]([C:36](=[N:34][O:32][CH2:29][CH3:30])[CH2:41][CH3:40])=[C:18]([OH:23])[CH2:17]1

Participants

5

Reactant 3

HCID 218852-DimethylaminopyridineHCID 31263Propionic anhydrideHCID 18696692HCID 18696692, compound

Product 1

HCID 136200006HCID 136200006, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of 9.3 g of the 5-(6-chloro-2-ethyl-2,4,7-trimethylindan-5-yl)-cyclohexane-1,3-dione in 50 ml of absolute toluene was added 15 ml of propionic anhydride. After refluxing for 4 hours, toluene and excess propionic anhydride were evaporated under reduced pressure to afford a residue. To the solution of the residue in 50 ml of toluene was added 0.6 g of dimethylaminopyridine and refluxed for 20 hours. The reaction mixture was evaporated under reduced pressure. The residue was purified by silica-gel column chromatography to afford 4.96 g of the title compound as yellow solid.

Workup

  1. temperatureAfter refluxing for 4 hours
  2. customtoluene and excess propionic anhydride were evaporated under reduced pressure
  3. customto afford a residue
  4. temperaturerefluxed for 20 hours
  5. customThe reaction mixture was evaporated under reduced pressure
  6. customThe residue was purified by silica-gel column chromatography

Sources & evidence

ORD record
ord-6b1f259d827c476eb2a52e3c5f3760ce
Source dataset
uspto-grants-2000_08
Patent number
US06096930

Reaction notes

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