반응 #69519

반응 방정식

Rochelle salt

toluene

ethyl 3-chloro-4-iodo-5-methoxybenzoate

diisobutyl aluminum hydride

→

title compound

수율 100.0%

(3-Chloro-4-iodo-5-methoxyphenyl)methanol

수율 100.0%

용매

ethyl acetate

반응 조건

후처리

1. 1
   workup.STIRRINGthe mixture was stirred
2. 2
   온도while warming to −30° C. for three hours
3. 3
   workup.STIRRINGthe mixture was stirred at room temperature for five hours
4. 4
   workup.STIRRINGAfter thoroughly shaking the mixture
5. 5
   기타the organic layer was separated
6. 6
   세척the organic layer was washed with brine
7. 7
   건조dried over anhydrous magnesium sulfate
8. 8
   여과The mixture was filtered
9. 9
   workup.DISTILLATIONthe solvent in the filtrate was distilled off under reduced pressure

실험 절차

To a mixture of ethyl 3-chloro-4-iodo-5-methoxybenzoate (15.6 g, 45.8 mmol) and toluene (150 mL), was added diisobutyl aluminum hydride (1.01M toluene solution: 95.2 mL, 96.2 mmol) while stirring at −78° C., and the mixture was stirred while warming to −30° C. for three hours. To the mixture, an aqueous solution (400 mL) of Rochelle salt (potassium sodium (+)-tartrate tetrahydrate) (77.6 g, 275 mmol) was added, the mixture was stirred at room temperature for five hours, followed by addition of ethyl acetate. After thoroughly shaking the mixture, the organic layer was separated, and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The mixture was filtered, and then the solvent in the filtrate was distilled off under reduced pressure to obtain the title compound (13.7 g, 45.8 mmol).

출처