Reacción #75447

Ecuación de reacción

Epibromohydrin

dimethylallyl alcohol

sodium hydride

→

title product

3,3-Dimethylallylglycidyl Ether

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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).

Fuente