Реакция #1605859

Уравнение реакции

hydrogen chloride

(1S)-4-bromo-2,3-dihydro-1H-inden-1-ol

sodium hydrogen carbonate

→

title compound

2-(((S)-4-bromo-2,3-dihydro-1H-inden-1-yl)oxy)tetrahydro-2H-pyran

Растворители

1,4-dioxane

methylene chloride

3,4-dihydro-2H-pyran

Условия реакции

Обработка

1. 1
   Другоеcould be obtained by a known method
2. 2
   workup.ADDITIONwas added
3. 3
   ДругоеThe resultant reaction mixture
4. 4
   Экстракцияextracted with methylene chloride (60 mL)
5. 5
   ПромывкаThe organic phase was washed with brine (60 mL)
6. 6
   Сушкаdried over anhydrous sodium sulfate
7. 7
   workup.DISTILLATIONFrom the organic phase, the solvent was distilled off under reduced pressure
8. 8
   Другоеthe resultant residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=95:5)
9. 9
   workup.DISTILLATIONFrom the eluted solution, the solvent was distilled off under reduced pressure

Методика

In methylene chloride (16.2 mL), 3,4-dihydro-2H-pyran (10.6 mL) was dissolved. To the solution, a solution of 4M hydrogen chloride in 1,4-dioxane (31.1 μL) was added and (1S)-4-bromo-2,3-dihydro-1H-inden-1-ol (10.0 g) that was commercially available or could be obtained by a known method was added. The resultant reaction mixture was stirred at room temperature for 3 hours. To the reaction mixture, a saturated aqueous sodium hydrogen carbonate solution (60 mL) was added and extracted with methylene chloride (60 mL). The organic phase was washed with brine (60 mL) and dried over anhydrous sodium sulfate. From the organic phase, the solvent was distilled off under reduced pressure and the resultant residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=95:5). From the eluted solution, the solvent was distilled off under reduced pressure to give the title compound (15 g).

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