Реакция #310854

Уравнение реакции

methanesulphonyl chloride

diethyl ether

octyn-1-ol

butyl lithium

diethyl ether

water

→

subtitle compound

8-(tetrahydropyran-2-yloxy)-1-methanesulphonyloxy-2-octyne

Растворители

hexane

Условия реакции

Обработка

1. 1
   workup.STIRRINGstirred at 0° C. for 3 hours
2. 2
   Экстракцияextracted with diethyl ether
3. 3
   Промывкаthe extract was washed with a saturated aqueous solution of sodium chloride
4. 4
   Сушкаdried over magnesium sulphate
5. 5
   Концентрированиеconcentrated under reduced pressure
6. 6
   ДругоеThe residue was purified by column chromatography on silica gel using
7. 7
   workup.ADDITIONa mixture of ethyl acetate and hexane (3:7) as eluent

Методика

Under an atmosphere of nitrogen, a solution of 4.2 g of the octyn-1-ol compound (prepared as described above) in 10 ml of diethyl ether was added dropwise to 12.8 ml of an 1.45 M solution of butyl lithium in hexane at 0° C., the mixture was stirred at 0° C. for 30 minutes. To the solution was added dropwise a solution of 1.58 ml of methanesulphonyl chloride in 7 ml of diethyl ether, then stirred at 0° C. for 3 hours. The mixture was poured into cold water, extracted with diethyl ether, the extract was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of ethyl acetate and hexane (3:7) as eluent to give 4.1 g of the subtitle compound having the following physical characteristics:

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