반응 #1339

반응 방정식

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

용매

dimethyl formamide

반응 조건

후처리

1. 1
   온도by external cooling under a nitrogen atmosphere
2. 2
   온도external cooling
3. 3
   기타was removed
4. 4
   기타the reaction quenched by the dropwise addition of saturated aqueous ammonium chloride solution
5. 5
   기타The mixture was then partitioned between water and diisopropyl ether
6. 6
   기타the aqueous phase separated
7. 7
   세척washed with diisopropyl ether (3×25 ml)
8. 8
   세척The organic phase was washed with brine
9. 9
   건조dried over anhydrous sodium sulphate
10. 10
    농축concentrated by evaporation under reduced pressure
11. 11
    기타After purification by a procedure similar to

실험 절차

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.

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