Water → HCID 9886753, compound

HRID 840328Notes

Reaction equation

HRID 840328 reaction equation
[C:1]([CH:9]([C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH:18]=[O:19])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24]1([NH:30]O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O>C(O)C>[C:24]1([N:30]2[O:8][C:1]3([C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[O:19][CH:18]2[C:17]2[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=2[CH:9]3[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7518N-PhenylhydroxylamineHCID 10086174HCID 10086174, compound

Product 1

HCID 9886753HCID 9886753, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 2.68 g quantity (10 mmols) of 1,2-diphenylindene, a known compound, was oxidized with ozone in 15 ml of methylene chloride, and the resulting reaction mixture was reduced with 2,77 g of triphenylphosphine in 30 ml of benzene at room temperature for 15 hours to obtain 1.8 g of 2-(α-benzoylbenzyl)benzaldehyde (yield 60%). A 300 mg portion (1 mmol) of the 2-(α-benzoylbenzyl)benzaldehyde was reacted with 109 mg of phenylhydroxylamine in 20 ml of ethanol at room temperature for 15 hours. The reaction mixture obtained was poured into water, followed by extraction with ether and then silica gel column chromatography for the separation of the product, consequently giving 117 mg of a 2:1 mixture of exo- and endo-isomers of the desired compound from a fraction obtained by elution with benzene-hexane (1:1) (yield 30%). The physical properties of the product are shown in Table 2.

Workup

  1. customThe reaction mixture obtained
  2. extractionfollowed by extraction with ether
  3. customsilica gel column chromatography for the separation of the product
  4. customconsequently giving
  5. addition117 mg of a 2:1 mixture of exo- and

Sources & evidence

ORD record
ord-1826ad88c2c64fc697468e24116b8235
Source dataset
uspto-grants-2002_04
Patent number
US06365610B1

Reaction notes

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