2,6-Di-(4-benzocyclobutenoxy)benzonitrile → HCID 178418598, compound

HRID 6193Notes

Reaction equation

HRID 6193 reaction equation
[CH:1]1[C:4]2[CH:5]=[CH:6][C:7]([O:9][C:10]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]4[CH:26]=[CH:25][C:22]5[CH:23]=[CH:24][C:21]=5[CH:20]=4)[C:11]=3[C:12]#[N:13])=[CH:8][C:3]=2[CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[CH:23]1[C:22]2[CH:25]=[CH:26][C:19]([O:18][C:14]3[CH:15]=[CH:16][CH:17]=[C:10]([O:9][C:7]4[CH:6]=[CH:5][C:4]5[CH:1]=[CH:2][C:3]=5[CH:8]=4)[C:11]=3[CH2:12][NH2:13])=[CH:20][C:21]=2[CH:24]=1

Participants

4

Reactant 2

HCID 197951102,6-Di-(4-benzocyclobutenoxy)benzonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 178418598HCID 178418598, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In a 500 ml, 4-necked round-bottomed flask equipped with an overhead mechanical stirrer, a thermometer/adaptor, a reflux condensor and a funnel was added 2,6-di-(4-benzocyclobutenoxy)benzonitrile followed by 260 ml of anhydrous diethyl ether. The resultant mixture was placed in an ice bath and stirred under anitrogen atmosphere. When the internal temperature reached 0° C., lithium aluminum hydride was added through the attached funnel in 3 portions (0.69 g, 0.96 g, 0.50 g), each addition followed by washing the funnel with about 10 ml Et2O, over a period of 15 minutes. The resulting mixture was stirred at 0° C. for 20 minutes, then the ice bath was removed and the mixture was allowed to warm to room temperature. The reaction mixture was then refluxed gently for 17 hours.

Workup

  1. customIn a 500 ml, 4-necked round-bottomed flask equipped with an overhead mechanical stirrer
  2. customreached 0° C.
  3. additioneach addition
  4. washby washing the funnel with about 10 ml Et2O
  5. stirringThe resulting mixture was stirred at 0° C. for 20 minutes
  6. customthe ice bath was removed
  7. temperatureThe reaction mixture was then refluxed gently for 17 hours

Sources & evidence

ORD record
ord-2e9e9e922e064d3ba03f213d5729e9eb
Source dataset
uspto-grants-1993_09
Patent number
US05247057

Reaction notes

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