Реакция #75447

Уравнение реакции

Epibromohydrin

dimethylallyl alcohol

sodium hydride

→

title product

3,3-Dimethylallylglycidyl Ether

Растворители

THF

Условия реакции

Обработка

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature for 24 hours
2. 2
   ДругоеTHF was removed on a rotary evaporator
3. 3
   Фильтрацияfiltered
4. 4
   КонцентрированиеThe ether solution was concentrated on a rotary evaporator
5. 5
   Другоеthe brown oil obtained
6. 6
   workup.DISTILLATIONwas distilled under vacuum

Методика

To a solution of dimethylallyl alcohol (17.3 g, 20.5 mL, 0.2 mol) in dry THF (200 mL), sodium hydride (4.8 g, 0.2 mol) was added in portions and the mixture was stirred at room temperature for 1 hour. Epibromohydrin (27.4 g, 17.12 mL, 0.2 mol) was added to this reaction mixture dropwise and the mixture was stirred at room temperature for 24 hours. THF was removed on a rotary evaporator and the residue was taken up in ether and filtered. The ether solution was concentrated on a rotary evaporator and the brown oil obtained was distilled under vacuum to yield the title product. bp. 93-94° C./10 mm. Yield: 17.2 g (60.5%). 1H NMR (CDCl3) δ1.68 and 1.75 (s, 6H, CH3), 2.61 and 2.88 (dd,2H, oxirane CH2), 3.17 (m, 1H, oxirane CH), 3.38 and 3.7 (m, 2H, CH2OCH2CH), 4.05 (m, 2H, CH2OCH2CH), 5.35 .(m, 1H, >C═CH).

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