반응 #2289441

반응 방정식

Borane THF

trans-2-(ethoxycarbonyl)cyclopropanecarboxylic acid

tert-butylchlorodiphenylsilane

imidazole

→

ethyl trans-2-((tert-butyldiphenylsilyloxy)methyl)cyclopropanecarboxylate

수율 79.0%

용매

THF

water

MeOH

반응 조건

후처리

1. 1
   농축The reaction mixture was concentrated under reduced pressure
2. 2
   workup.DISSOLUTIONThe residue was dissolved in DMF (50 mL)
3. 3
   workup.STIRRINGthe mixture was stirred for 5 hr
4. 4
   추출the mixture was extracted with ethyl acetate
5. 5
   세척The organic layer was washed with water and brine
6. 6
   건조dried over magnesium sulfate
7. 7
   농축concentrated under reduced pressure
8. 8
   기타the obtained residue was purified by silica gel column chromatography (solvent gradient; 2→35% ethyl acetate/hexane)

실험 절차

1M Borane-THF complex THF solution (85 mL, 84.98 mmol) was added to a solution of trans-2-(ethoxycarbonyl)cyclopropanecarboxylic acid (11.2 g, 70.82 mmol) in THF (100 mL) at 0° C., and the mixture was stirred overnight at room temperature. MeOH was added thereto, and then the gas was not generated. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in DMF (50 mL), tert-butylchlorodiphenylsilane (20.10 mL, 84.98 mmol) and imidazole (5.79 g, 84.98 mmol) were added thereto, and the mixture was stirred for 5 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate, and concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (solvent gradient; 2→35% ethyl acetate/hexane) to give ethyl trans-2-((tert-butyldiphenylsilyloxy)methyl)cyclopropanecarboxylate (21.40 g, 55.9 mmol, 79%) as a colorless oil.

출처