تفاعل #3108

معادلة التفاعل

Sodium t-butoxide

1-bromo-1-chloro-2,2,2-trifluoroethane

3-methylbut-1-en-1-al

tetrahydrofuran

→

5-bromo-5-chloro-4-hydroxy-2-methyl-6,6,6-trifluorohex-2-ene

المذيبات

dimethyl formamide

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةby external cooling under a nitrogen atmosphere
2. 2
   درجة الحرارةexternal cooling
3. 3
   أخرىwas removed
4. 4
   أخرىthe reaction quenched by the dropwise addition of saturated aqueous ammonium chloride solution
5. 5
   أخرىThe mixture was then partitioned between water and diisopropyl ether
6. 6
   أخرىthe aqueous phase separated
7. 7
   غسيلwashed with diisopropyl ether (3×25 ml)
8. 8
   غسيلThe organic phase was washed with brine
9. 9
   تجفيفdried over anhydrous sodium sulphate
10. 10
    تركيزconcentrated by evaporation under reduced pressure
11. 11
    أخرىAfter purification by a procedure similar to

الإجراء التجريبي

Sodium t-butoxide (1.39 g of a 42% solution in dry dimethyl formamide was added dropwise over a period of 5 minutes to a stirred mixture of 1-bromo-1-chloro-2,2,2-trifluoroethane (0.535 ml), 3-methylbut-1-en-1-al (0.538 ml) and dry tetrahydrofuran (10 ml) maintained at a temperature of -78° C. by external cooling under a nitrogen atmosphere. The mixture was then stirred for a further 40 minutes at the temperature after which the external cooling was removed and the reaction quenched by the dropwise addition of saturated aqueous ammonium chloride solution. The mixture was then partitioned between water and diisopropyl ether and the aqueous phase separated, washed with diisopropyl ether (3×25 ml), and the washings combined with the organic phase. The organic phase was washed with brine and dried over anhydrous sodium sulphate and concentrated by evaporation under reduced pressure. After purification by a procedure similar to that set out in the previous Example there was obtained 5-bromo-5-chloro-4-hydroxy-2-methyl-6,6,6-trifluorohex-2-ene (1.39 g), identified by nuclear magnetic resonance and infra-red spectroscopy.

المصدر