반응 #2640

반응 방정식

tert-butyl methyl ether

4-tert-butyldimethylsiloxy-2-cyclopentenone

MgBr2

lithium aluminum hydride

lithium aluminum hydride

→

title compound

수율 64.4%

cis-4-tert-butyldimethylsilyloxy-2-cyclopentenol

수율 64.4%

용매

toluene

반응 조건

후처리

1. 1
   기타overnight
2. 2
   기타at room temperature
3. 3
   workup.STIRRINGthe reaction is stirred for 2 hours
4. 4
   기타The reaction is then quenched by slow addition of 1N NaOH (5 mL)
5. 5
   여과followed by filtration through diatomaceous earth
6. 6
   건조The filtrate is dried over anhydrous magnesium sulfate
7. 7
   여과filtered
8. 8
   농축concentrated under vacuum

실험 절차

A stirred solution of 4-tert-butyldimethylsiloxy-2-cyclopentenone (2.0 g, 9.42 mmol) in anhydrous toluene (15 mL) under an atmosphere of argon is treated with MgBr2 (3.5 g, 19.0 mol). The mixture is cooled to -25° C. and treated with lithium aluminum hydride (178 mg, 4.69 mmol) in one portion, followed by addition of anhydrous tert-butyl methyl ether (3.0 mL). The reaction is stirred at -20° C. for 2 hours and then overnight at room temperature. Additional lithium aluminum hydride (178 mg, 4.69 mmol) is added at room temperature and the reaction is stirred for 2 hours. The reaction is then quenched by slow addition of 1N NaOH (5 mL) followed by filtration through diatomaceous earth. The filtrate is dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum to provide the title compound (1.3 g); cis/trans/1-2 +1-4 addition, 90/3/7.

출처