Diethyl Ether → 1-(4-Bromobutyldimethylsilyl)-1-propyne

HRID 1762720Notes

Reaction equation

HRID 1762720 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][Si:6]([CH3:9])([CH3:8])Cl.[C:10]([Li])#[C:11]C.[CH2:14](OCC)C>>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][Si:6]([CH3:9])([CH3:14])[C:8]#[C:10][CH3:11]

Participants

4

Conditions

Temperature
25 °C

Procedure

This novel monomer was synthesized by adding 6.7 g (0.029 mole) of 4-bromobutyldimethylchlorosilane dropwise at 0° C. to a stirred solution of propynyllithium (1.34 g, 0.029 mole) in 50 ml of dry diethyl ether. The reaction mixture was stirred overnight at 25° C. and then poured into 400 ml of ice water. The ether layer was washed with distilled water, separated, and dried over MgSO4. The ether layer was then filtered and the product separated by removing the ether using a rotovapor. The resulting oil was purified by vacuum distillation and had a b.p. of 70°-75° C. at 15 mm Hg pressure. Yield was 75% of theoretical. 'H NMR confirmed the structure.

Workup

  1. customThis novel monomer was synthesized
  2. washThe ether layer was washed with distilled water
  3. customseparated
  4. dry with materialdried over MgSO4
  5. filtrationThe ether layer was then filtered
  6. customthe product separated
  7. customby removing the ether using a rotovapor
  8. distillationThe resulting oil was purified by vacuum distillation

Sources & evidence

ORD record
ord-f00bb330070343ccbab9ad1a25432498
Source dataset
uspto-grants-1989_05
Patent number
US04833262

Reaction notes

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