反応 #482012

反応方程式

3-buten-1-ol

pyridine

tert-butyldimethylsilyl chloride

→

product

収率 56.3%

4-[(Tert-Butyldimethylsilyl)oxy]-1-butene

収率 56.3%

溶媒

methylene chloride

反応条件

後処理

1. 1
   その他The ice-bath was removed
2. 2
   workup.ADDITIONThe mixture, containing a white precipitate
3. 3
   workup.ADDITIONwas poured into water (60 mL)
4. 4
   workup.STIRRINGshaken
5. 5
   その他The methylene chloride layer was separated from the aqueous layer
6. 6
   抽出the aqueous layer extracted with methylene chloride (30 mL)
7. 7
   洗浄washed twice with water
8. 8
   乾燥dried (Na2SO4)
9. 9
   ろ過filtered
10. 10
    その他evaporated
11. 11
    その他to give 8.94 g of crude product
12. 12
    workup.DISTILLATIONVacuum distillation
13. 13
    その他afforded several fractions
14. 14
    その他the fraction with bp 80-82° C. at 35 mm Hg was collected

実験手順

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).

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