2-Dimethylaminopyridine → HCID 136149643, compound

HRID 1870635Notes

Reaction equation

HRID 1870635 reaction equation
[Cl:1][C:2]1[C:10]([CH3:11])=[C:9]2[C:5]([CH2:6][C:7]([CH3:13])([CH3:12])[CH2:8]2)=[C:4]([CH3:14])[C:3]=1[CH:15]1[CH2:20][C:19](=[O:21])[CH2:18][C:17](=[O:22])[CH2:16]1.C(O[C:28](=[O:31])[CH2:29]C)(=O)CC.C[N:33]([C:35]1[CH:40]=[CH:39][CH:38]=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]([CH3:13])([CH3:12])[CH2:8]2)=[C:4]([CH3:14])[C:3]=1[CH:15]1[CH2:20][C:19](=[O:21])[C:18]([C:35](=[N:33][O:31][CH2:28][CH3:29])[CH2:40][CH2:39][CH3:38])=[C:17]([OH:22])[CH2:16]1

Participants

5

Reactant 3

HCID 218852-DimethylaminopyridineHCID 31263Propionic anhydrideHCID 18696679HCID 18696679, compound

Product 1

HCID 136149643HCID 136149643, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of 8.02 g of the 5-(6-chloro-2,2,4,7-tetramethylindan-5-yl)-cyclohexane-1,3-dione in 100 ml of absolute toluene was added 12.8 ml of propionic anhydride. After refluxing for 4 hours, toluene and excess propionicanhydride were evaporated under reduced pressure to afford a residue. To the solution of the residue in 100 ml of toluene was added 0.61 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 10.1 g of the title compound as yellow solid.

Workup

  1. temperatureAfter refluxing for 4 hours
  2. customtoluene and excess propionicanhydride 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-a35f5dea92a94861b1c2c40d5726a92c
Source dataset
uspto-grants-2000_08
Patent number
US06096930

Reaction notes

Loading…