Butyric anhydride → HCID 136149643, compound

HRID 1870636Notes

Reaction equation

HRID 1870636 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:23](OC(=O)CCC)(=[O:27])[CH2:24]CC.CN(C1[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=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:39](=[N:38][O:27][CH2:23][CH3:24])[CH2:40][CH2:41][CH3:42])=[C:17]([OH:22])[CH2:16]1

Participants

5

Reactant 3

HCID 7798Butyric anhydrideHCID 218852-DimethylaminopyridineHCID 18696679HCID 18696679, compound

Product 1

HCID 136149643HCID 136149643, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution 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 13.4 ml of butyric 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 0.61 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 3.51 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-71e462384e004dba9a0d6187a34631ef
Source dataset
uspto-grants-2000_08
Patent number
US06096930

Reaction notes

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