HCID 10316940, compound → HCID 10155767, compound

HRID 399235Notes

Reaction equation

HRID 399235 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]3[C:18]4[C:13](=[CH:14][C:15]([O:19][CH2:20][CH2:21][CH3:22])=[CH:16][CH:17]=4)[C:12](=[O:23])[CH:11]3[C:24]([O:26][CH3:27])=[O:25])=[CH:4][C:3]=2[O:2]1>C1(C)C=CC=CC=1>[CH3:27][O:26][C:24]([C:11]1[C:12](=[O:23])[C:13]2[C:18]([C:10]=1[C:5]1[CH:6]=[CH:7][C:8]3[O:9][CH2:1][O:2][C:3]=3[CH:4]=1)=[CH:17][CH:16]=[C:15]([O:19][CH2:20][CH2:21][CH3:22])[CH:14]=2)=[O:25]

Participants

3

Reactant 1

HCID 10316940HCID 10316940, compound

Product 1

HCID 10155767HCID 10155767, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Methyl(1RS,2SR)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)-3-oxo-indane-2-carboxylate (26.2 g, 71 mmol) was dissolved in toluene (250 mL) and DDQ (dichlorodicyano-quinone) (16.5 g, 71 mmol) was added. The mixture was heated at 80° C. for 2 h. then cooled, filtered and the solvent removed in vacuo. The product was purified by flash column chromatography on silica gel (eluant: EtOAc/hexane, 20:80) to give the title compound as an orange solid (11.3 g, 44 %); m.p. 125°-126° C. Anal. Calc. for C21H18O6 : C, 68.85; H, 4.95. Found: C, 68.45; H, 4.97.

Workup

  1. temperaturethen cooled
  2. filtrationfiltered
  3. customthe solvent removed in vacuo
  4. customThe product was purified by flash column chromatography on silica gel (eluant: EtOAc/hexane, 20:80)

Sources & evidence

ORD record
ord-db480bcef0f74c5f8adb2ffcd25bf423
Source dataset
uspto-grants-1998_10
Patent number
US05817693

Reaction notes

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