HCID 19703033, compound → (4-Aminobut-1-yn-1-yl)trimethylsilane

HRID 1777521Notes

Reaction equation

HRID 1777521 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]([CH2:10][CH2:11][C:12]#[C:13][Si:14]([CH3:17])([CH3:16])[CH3:15])=[N+]=[N-]>C(OCC)C>[CH3:15][Si:14]([CH3:17])([CH3:16])[C:13]#[C:12][CH2:11][CH2:10][NH2:7]

Participants

4

Reactant 2

HCID 19703033HCID 19703033, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19703099(4-Aminobut-1-yn-1-yl)trimethylsilaneYield 60%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Lithium aluminium hydride (0.095 g; 2.51 mmol) was added to a mixture of (4-azidobut-1-ynyl)trimethylsilane (0.700 g; 4.18 mmol) in diethyl ether. The resulting mixture was stirred at room temperature for two hours and carefully quenched with water and sodium hydroxide (10% in water). The aqueous layer was extracted with diethyl ether dried over magnesium sulfate, and concentrated under reduced pressure to yield 0.349 g (60%) of 4-(trimethylsilyl)but-3-yn-1-amine.

Workup

  1. customcarefully quenched with water and sodium hydroxide (10% in water)
  2. extractionThe aqueous layer was extracted with diethyl ether
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-10dad21c549844db8d095f0ea48232d2
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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