Dimethylformamide → HCID 15116868, compound

HRID 1461635Notes

Reaction equation

HRID 1461635 reaction equation
[O:1]1[CH2:17][C:2]1([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:3][C:4]1([CH2:15][CH3:16])[C:12](=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]1=[O:14].CN(C)C=O.[BrH:29].N1C=CC=CC=1>C(Cl)(Cl)Cl.O>[Br:29][CH2:17][C:2]([OH:1])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:3][C:4]1([CH2:15][CH3:16])[C:12](=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]1=[O:14]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 87810Pyridine, hydrobromide (1:1)HCID 151168752-(2,3-Epoxy-2-phenylpropyl)-2-ethylindan-1,3-dione

Product 1

HCID 15116868HCID 15116868, compoundYield 23.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

To the mixture of 1.53 g of 2-(2,3-epoxy-2-phenylpropyl)-2-ethylindan-1,3-dione, 15 ml of chloroform and 1 ml of dimethylformamide, was added 0.96 g of pyridine hydrobromide. After refluxing under heating for 6 hours, the reaction mixture was poured into water and was added 20 ml of chloroform. The organic layer was washed with water and with a saturated saline solution, and dried over anhydrous magnesium sulfate. After evaporating the solvent, the residue was separated and purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate=4/1) to obtain 0.45 g of the compound No. 36 shown in Table 2.

Workup

  1. temperatureAfter refluxing
  2. temperatureunder heating for 6 hours
  3. washThe organic layer was washed with water and with a saturated saline solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter evaporating the solvent
  6. customthe residue was separated
  7. custompurified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-93a4677476e1448c8c8b0150e56d59e7
Source dataset
uspto-grants-1991_12
Patent number
US05076830

Reaction notes

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