Pyridine → (But-3-enyloxy)(tert-butyl)dimethylsilane

HRID 1268237Notes

Reaction equation

HRID 1268237 reaction equation
[CH2:1]([OH:5])[CH2:2][CH:3]=[CH2:4].N1C=CC=CC=1.[Si:12](Cl)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]>C(Cl)Cl>[Si:12]([O:5][CH2:1][CH2:2][CH:3]=[CH2:4])([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 1049PyridineHCID 28928tert-Butyldimethylsilyl chlorideHCID 693893-Buten-1-ol

Product 1

HCID 10008065(But-3-enyloxy)(tert-butyl)dimethylsilaneYield 56.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under a nitrogen atmosphere, to a cold (0° C.), stirring solution of 3-buten-1-ol (2.16 g, 30.0 mmol), pyridine (9 mL), and methylene chloride (30 mL) was added tert-butyldimethylsilyl chloride (4.53 g, 30.1 mmol) purchased from Aldrich Chemical Company. The ice-bath was removed and the mixture was allowed to stir 1 h at room temperature. The mixture, containing a white precipitate, was poured into water (60 mL) and shaken. The methylene chloride layer was separated from the aqueous layer, and the aqueous layer extracted with methylene chloride (30 mL). The two resulting organic extracts were combined, washed twice with water, dried (Na2SO4), filtered, and evaporated to give 8.94 g of crude product. Vacuum distillation afforded several fractions, the fraction with bp 80-82° C. at 35 mm Hg was collected to give 3.14 g (56.3%) of product as an oil. 1H NMR (CDCl3): δ 5.86-5.73 (m, 1H), 5.08-4.98 (m, 2H), 3.64 (t, 2H), 2.29-2.22 (m, 2H), 0.87 (s, 9H), 0.03 (s, 6H).

Workup

  1. customThe ice-bath was removed
  2. additionThe mixture, containing a white precipitate
  3. additionwas poured into water (60 mL)
  4. stirringshaken
  5. customThe methylene chloride layer was separated from the aqueous layer
  6. extractionthe aqueous layer extracted with methylene chloride (30 mL)
  7. washwashed twice with water
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. customevaporated
  11. customto give 8.94 g of crude product
  12. distillationVacuum distillation
  13. customafforded several fractions
  14. customthe fraction with bp 80-82° C. at 35 mm Hg was collected

Sources & evidence

ORD record
ord-391bcaa3c5104d6289bc271b2626b404
Source dataset
uspto-grants-2003_04
Patent number
US06555684B2

Reaction notes

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