HCID 18173787, compound → HCID 18173862, compound

HRID 1634817Notes

Reaction equation

HRID 1634817 reaction equation
[C:1]([Si:5]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[O:6][C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[C:9]([F:15])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[C:1]([Si:5]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[O:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11][NH2:12])=[C:9]([F:15])[CH:8]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 18173787HCID 18173787, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18173862HCID 18173862, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of the 4-(t-butyl-diphenyl-silanyloxy)-2-fluoro-benzonitrile (2.07 g, 5.52 mmol) in ether (17 mL) was added a solution of lithium aluminum hydride (6.6 mL, 1M in THF) slowly. The reaction was heated at reflux for two hours and allowed to stir overnight at ambient temperature. The reaction was quenched with 1.17 mL of water, then 1.17 mL of NaOH (15%), and 1.17 mL of water. The white solid was filtered, washed with methylene chloride. The filtrate was dried (Na2SO4), and concentrated in vacuo to give the benzylamine (1.66 g,) as a yellow oil, which was used directly in the next step.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for two hours
  3. customThe reaction was quenched with 1.17 mL of water
  4. filtrationThe white solid was filtered
  5. washwashed with methylene chloride
  6. dry with materialThe filtrate was dried (Na2SO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4a48aa8165744ad6b4e459cbbd6ec0a8
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

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