Pyridine → Silane, (6-bromo-1-hexynyl)trimethyl-

HRID 2352502Notes

Reaction equation

HRID 2352502 reaction equation
[CH3:1][Si:2]([CH3:11])([CH3:10])[C:3]#[C:4][CH2:5][CH2:6][CH2:7][CH2:8]O.N1C=CC=CC=1.P(Br)(Br)[Br:19]>C(OCC)C>[CH3:1][Si:2]([CH3:11])([CH3:10])[C:3]#[C:4][CH2:5][CH2:6][CH2:7][CH2:8][Br:19]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24614Phosphorus tribromideHCID 10877568HCID 10877568, compound

Product 1

HCID 11053532Silane, (6-bromo-1-hexynyl)trimethyl-Yield 125.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a mixture of 1-trimethylsilyl(hex-1-yn-6-ol) (32.6 g, 190 mmol) and pyridine (0.38 mL) dissolved in diethyl ether (100 mL) was added slowly phosphorus tribromide (7.1 mL, 75 mmol) in diethyl ether (20 mL). Upon addition a precipitate formed and the heterogeneous solution was stirred at room temperature overnight. The mixture was then heated at reflux for 2.5 hours and, upon cooling, was poured onto ice, washed with water, sodium bicarbonate solution, brine and dried (MgSO4). Evaporation of solvent under reduced pressure gave a residue which was distilled (b.p. 80° C., 3.5 mm Hg) to give 22 g (50%) of product. 1H NMR (CDCl3) δ: 0.14 (s, 9H), 1.64-1.72 (quintet, 2H), 1.91-2.02 (quintet, 2H), 2.27 (t, 2H), 3.44 (t, 2H) ppm.

Workup

  1. additionUpon addition a precipitate
  2. customformed
  3. temperatureThe mixture was then heated
  4. temperatureat reflux for 2.5 hours
  5. temperatureupon cooling
  6. additionwas poured onto ice
  7. washwashed with water, sodium bicarbonate solution, brine
  8. dry with materialdried (MgSO4)
  9. customEvaporation of solvent under reduced pressure
  10. customgave a residue which
  11. distillationwas distilled (b.p. 80° C., 3.5 mm Hg)

Sources & evidence

ORD record
ord-acd477e4cfe2484cbaa27803dce1b600
Source dataset
uspto-grants-1989_10
Patent number
US04877779

Reaction notes

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