Toluene → HCID 18696707, compound

HRID 1870650Notes

Reaction equation

HRID 1870650 reaction equation
[Cl:1][C:2]1[C:3]([CH:16]2[CH2:21][C:20](=[O:22])[CH2:19][C:18](=[O:23])[CH2:17]2)=[C:4]([CH3:15])[C:5]([CH3:14])=[C:6]2[C:10]=1[CH2:9][C:8]([CH2:12][CH3:13])([CH3:11])[CH2:7]2.CN([C:27]1[CH:32]=CC=CN=1)C.[C:33]1(C)C=CC=C[CH:34]=1>>[Cl:1][C:2]1[C:3]([CH:16]2[CH2:21][C:20](=[O:22])[C:19]([C:18](=[O:23])[CH2:17][CH2:33][CH3:34])=[CH:32][CH2:27]2)=[C:4]([CH3:15])[C:5]([CH3:14])=[C:6]2[C:10]=1[CH2:9][C:8]([CH2:12][CH3:13])([CH3:11])[CH2:7]2

Participants

4

Reactant 3

HCID 1140Toluene2×HCID 218852-DimethylaminopyridineHCID 18696705HCID 18696705, compound

Product 1

HCID 18696707HCID 18696707, compoundYield 53%

Procedure

To a solution 7.12 g of the 5-(7-chloro-2-ethyl-2,4,5-trimethylindan-6-yl)-cyclohexane-1,3-dione in 70 ml of absolute toluene was added 15 ml of buryric anhydride. After refluxing for 4 hours, toluene and excess butyric anhydride were evaporated under reduced pressure to afford a residue. To the solution of the residue in 100 ml of toluene was added 0.56 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 4.64 g of the title compound as yellow solid.

Workup

  1. temperatureAfter refluxing for 4 hours
  2. customtoluene and excess butyric 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-ade8339927fb4378ac7288792f3fc38d
Source dataset
uspto-grants-2000_08
Patent number
US06096930

Reaction notes

Loading…