反応 #165395

反応方程式

ethoxymethyl chloride

Tributyltin hydride

ammonium chloride

n-butyl lithium

diisopropylamine

→

title compound

収率 66.8%

Tributyl-ethoxymethyl-tin

収率 66.8%

溶媒

diethyl ether

tetrahydrofuran

反応条件

後処理

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

実験手順

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%).

出典