Реакция #40289

Уравнение реакции

lithiumacetylid ethylendiamin

diisopropylethylamine

dichlorodiisopropylsilane

benzyl alcohol

→

Compound 14a

Выход 41.0%

Benzyloxy-ethynyl-diisopropyl-silane

Выход 41.0%

Растворители

Water

THF

THF

Условия реакции

Обработка

1. 1
   ТемператураThe mixture was cooled down to −78° C.
2. 2
   workup.STIRRINGThe reaction mixture was stirred for 5 h (−78→20° C.)
3. 3
   ЭкстракцияThe mixture was extracted with dichloromethane (20 mL)
4. 4
   СушкаThe organic phase was dried (Na2SO4)
5. 5
   Концентрированиеconcentrated

Методика

A solution of benzyl alcohol (0.1 mL, 1.0 mmol) in THF (0.5 mL) was added dropwise to a cooled (−78° C.) solution of diisopropylethylamine (1 mL), dichlorodiisopropylsilane (0.3 mL, 1.62 mmol) in THF (4 mL). The solution was stirred for 3 h (−78→−20° C.). The mixture was cooled down to −78° C. and lithiumacetylid-ethylendiamin-complex (250 mg, 2.71 mmol) was added. The reaction mixture was stirred for 5 h (−78→20° C.). Water (4 mL) was added. The mixture was extracted with dichloromethane (20 mL). The organic phase was dried (Na2SO4) and concentrated. Compound 14a (100 mg, 41%) was obtained after flash chromatography. 1H-NMR (CDCl3): δ 7.4 (5H, 5×HC═), 5.0 (2H, CH2), 2.6 (1H, CH), 1.0 (14H, 2×CH, 2×CH3).

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