Sodium Azide → (4-Azidobut-1-ynyl)triethylsilane

HRID 58640Notes

Reaction equation

HRID 58640 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].CC1C=CC(S(O[CH2:16][CH2:17][C:18]#[C:19][Si:20]([CH2:25][CH3:26])([CH2:23][CH3:24])[CH2:21][CH3:22])(=O)=O)=CC=1>CN(C=O)C>[N:1]([CH2:16][CH2:17][C:18]#[C:19][Si:20]([CH2:25][CH3:26])([CH2:21][CH3:22])[CH2:23][CH3:24])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 120301384-(Triethylsilyl)but-3-yn-1-yl 4-methylbenzene-1-sulfonate

Product 1

HCID 86663839(4-Azidobut-1-ynyl)triethylsilaneYield 103.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Sodium azide (1.80 g; 27.65 mmol) was added to a solution of 4-(triethylsilyl)but-3-ynyl 4-methylbenzenesulfonate (3.12 g; 9.22 mmol) in DMF (15 mL) and stirred at 60° C. for 3 hours. After cooling, the volatiles were removed under reduced pressure and the residue was partitioned between saturated ammonium chloride and ethyl acetate. The organic layer was dried and concentrated under reduced pressure to afford 2.0 g (quantitative yield) of (4-azidobut-1-ynyl)triethylsilane as a colorless oil.

Workup

  1. temperatureAfter cooling
  2. customthe volatiles were removed under reduced pressure
  3. customthe residue was partitioned between saturated ammonium chloride and ethyl acetate
  4. customThe organic layer was dried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-83eb10e8740f4a2c89ba0f4d6f2e6b50
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Reaction notes

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