1-Tetradecyne → HCID 178442821, compound

HRID 264100Notes

Reaction equation

HRID 264100 reaction equation
[CH:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].C[Si]([N:19]=[N+:20]=[N-:21])(C)C>>[CH2:12]([C:13]1[N:19]=[N:20][NH:21][CH:14]=1)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1]

Participants

3

Reactant 2

HCID 698231-TetradecyneHCID 78378Azidotrimethylsilane

Product 1

HCID 178442821HCID 178442821, compoundYield 50%

Procedure

A mixture of 1-tetradecyne (6.6 g, 34 mmol) and trimethylsilyl azide (4.1 g, 35 mmol) was autoclaved at 135° C. for 14 hours and then at 150° C. for 14 hours. The resulting mixture was rinsed with ether and the ether solution was washed with water, dried over MgSO4, filtered, and concentrated to give a brown oil. Triturated with cold hexanes to give the title compound as a tan solid (4.02 g, 50%); mp 64°-67° C.

Workup

  1. waitat 150° C. for 14 hours
  2. washThe resulting mixture was rinsed with ether
  3. washthe ether solution was washed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a brown oil
  8. customTriturated with cold hexanes

Sources & evidence

ORD record
ord-3bd0514f0996424f9321ac503c2497e4
Source dataset
uspto-grants-1997_07
Patent number
US05646170

Reaction notes

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