Diethyl Ether → HCID 9795013, compound

HRID 840329Notes

Reaction equation

HRID 840329 reaction equation
[CH3:1][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:3]1.[O:17]=[O+:18][O-].CC[O:22]CC>C(Cl)(Cl)(Cl)Cl>[CH3:1][CH:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[C:4]2([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[O:22][CH:3]1[O:17][O:18]2

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24823OzoneHCID 6098851-Methyl-3-phenyl-1H-indene

Product 1

HCID 9795013HCID 9795013, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A 1.03 g quantity (5 mmols) of 1-methyl-3-phenylindene, a known compound, was dissolved in 20 ml of carbon tetrachloride, and thereafter reacted with ozone in 1.3 times the molar quantity of the compound at 0° C. To the reaction mixture was added 50 ml of ether, and the organic layer was washed with saturated aqueous solution of sodium bicarbonate and then with saturated aqueous solution of sodium chloride. The organic layer obtained was dried over anhydrous magnesium sulfate, the solvent was thereafter distilled off in a vacuum, and the residue was subjected to silica gel column chromatography for separation and purification (eluent: benzene-hexane, 1:5), consequently giving 0.89 g (yield 70%) of a 2:1 mixture of exo- and endo-isomers of the desired compound. The two isomers were individually isolated by repeating column chromatography again and recrystallization from methanol. The physical properties of two isomeric products are shown in Table 1.

Workup

  1. washthe organic layer was washed with saturated aqueous solution of sodium bicarbonate
  2. customThe organic layer obtained
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. distillationthe solvent was thereafter distilled off in a vacuum
  5. customthe residue was subjected to silica gel column chromatography for separation and purification (eluent: benzene-hexane, 1:5)
  6. customconsequently giving
  7. addition0.89 g (yield 70%) of a 2:1 mixture of exo- and

Sources & evidence

ORD record
ord-0c34b9ce06a44ee29e3871875d739278
Source dataset
uspto-grants-2002_04
Patent number
US06365610B1

Reaction notes

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