Реакция #165395

Уравнение реакции

ethoxymethyl chloride

Tributyltin hydride

ammonium chloride

n-butyl lithium

diisopropylamine

→

title compound

Выход 66.8%

Tributyl-ethoxymethyl-tin

Выход 66.8%

Растворители

diethyl ether

tetrahydrofuran

Условия реакции

Обработка

1. 1
   workup.STIRRINGthe reaction mixture was stirred for 40 minutes at 0° C
2. 2
   ТемператураThe reaction mixture was raised to room temperature
3. 3
   Другоеthe organic layer was separated
4. 4
   ПромывкаThe organic layer was washed with saturated aqueous sodium chloride
5. 5
   Концентрированиеafter which the organic layer was concentrated under a reduced pressure
6. 6
   ДругоеThe residue was purified by neutral silica gel column chromatography (heptane: diethyl ether=30:1)

Методика

To a mixture of diisopropylamine (2.1 mL, 15 mmol) and tetrahydrofuran (30 mL) was added dropwise n-butyl lithium (2.4 M n-hexane solution, 5.0 mL, 12 mmol) at −78° C., and then the reaction mixture was stirred for 30 minutes. Tributyltin hydride (3.3 mL, 12 mmol) was added dropwise to this mixture at −78° C., and then the reaction mixture was stirred for 40 minutes at 0° C. The reaction mixture was cooled to −78° C., after which ethoxymethyl chloride (1.1 mL, 12 mmol) was added dropwise to the reaction mixture. The reaction mixture was raised to room temperature, diethyl ether and an ammonium chloride aqueous solution were added to the reaction mixture, and the organic layer was separated. The organic layer was washed with saturated aqueous sodium chloride, after which the organic layer was concentrated under a reduced pressure. The residue was purified by neutral silica gel column chromatography (heptane: diethyl ether=30:1) to obtain the title compound (2.8 g, 66%).

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