Acetylacetone → 3-(7-Methoxy-6-methyl-indan-4-ylmethyl)-pentane-2,4-dione

HRID 1099360Notes

Reaction equation

HRID 1099360 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[CH2:10][CH2:9][CH2:8][C:7]=2[C:6]([CH:12]=O)=[CH:5][C:4]=1[CH3:14].[C:15]([CH2:18][C:19](=[O:21])[CH3:20])(=[O:17])[CH3:16].[H][H]>C1(C)C=CC=CC=1.N1CCCCC1.C(O)(=O)C.CO.[Pd]>[CH3:1][O:2][C:3]1[C:4]([CH3:14])=[CH:5][C:6]([CH2:12][CH:18]([C:19](=[O:21])[CH3:20])[C:15](=[O:17])[CH3:16])=[C:7]2[C:11]=1[CH2:10][CH2:9][CH2:8]2

Participants

9

Reactant 3

HCID 31261AcetylacetoneHCID 771748277-Methoxy-6-methyl-indan-4-carbaldehydeHCID 178418361HCID 178418361, compound

Product 1

HCID 668129973-(7-Methoxy-6-methyl-indan-4-ylmethyl)-pentane-2,4-dioneYield 25.2%

Reagents, catalysts & solvents 5

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 1140TolueneSolventHCID 8082PiperidineSolvent

Procedure

To the solution of 7-Methoxy-6-methyl-indan-4-carbaldehyde (8.0 gm 0.042 mole) and Acetyl acetone (4.63 gm, 0.046 mole) in Toluene (80 ml), Piperidine (0.5 ml) and Acetic acid (0.5 ml) were added. The reaction mixture was refluxed over 3A° molecular sieve using dean stark apparatus for 24 hours. Toluene was distilled under vacuum to give a crude product, which was purified by column chromatography using 5% Ethyl acetate in Hexane. The fractions were distilled to give 3.0 gm of condensed product It was dissolved in Methanol (60 ml) and hydrogenation was carried out over 5% w/w Palladium on Barium sulphate (350 mg) at 40-50 psi. using Hydrogen gas at 25-30° C. The reaction mixture was filtered through hyflow bed and distilled under vacuum to give a 2.9 gm of desired compound as a viscous oil.

Workup

  1. temperatureThe reaction mixture was refluxed over 3A° molecular sieve
  2. customfor 24 hours
  3. distillationToluene was distilled under vacuum
  4. customto give a crude product, which
  5. customwas purified by column chromatography
  6. distillationThe fractions were distilled
  7. customto give
  8. custom3.0 gm of condensed product It
  9. customat 25-30° C
  10. filtrationThe reaction mixture was filtered through hyflow bed
  11. distillationdistilled under vacuum

Sources & evidence

ORD record
ord-0d836387610f4da99f1bf837610a4755
Source dataset
uspto-grants-2012_03
Patent number
US08143424B2

Reaction notes

Loading…