반응 #48668

반응 방정식

lithium aluminum hydride

tert-butanol

3-tert-butylcyclobutanone

hydride

→

title compound

Cis-3-tert-butylcyclobutanol

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.STIRRINGStir for 1 hour at −78° C.
2. 2
   기타Slowly quench the mixture with 0.1 N hydrochloric acid
3. 3
   workup.ADDITIONDilute the resulting mixture with ethyl acetate
4. 4
   workup.STIRRINGa saturated aqueous solution of sodium potassium tartrate (Rochelle salt) and stir the biphasic mixture overnight
5. 5
   여과Filter the mixture
6. 6
   기타to remove
7. 7
   기타precipitates
8. 8
   기타separate the aqueous layer
9. 9
   농축Saturate the aqueous phase with sodium chloride
10. 10
    추출extract with ethyl acetate
11. 11
    workup.ADDITIONAdd the
12. 12
    추출organic extract to the ethyl acetate solution of the reaction mixture
13. 13
    세척wash the resultant mixture with saturated aqueous sodium chloride solution
14. 14
    건조dry (magnesium sulfate)
15. 15
    여과filter
16. 16
    농축concentrate

실험 절차

Cool lithium aluminum hydride (16 mL, 16 mmol, 1.0 M solution in tetrahydrofuran) under a nitrogen atmosphere to 0° C. Add tert-butanol (4.6 mL, 48.1 mmol) dropwise, warm to room temperature, and stir the resulting solution for 1 hour. Cool the hydride solution to −78° C. and add a solution of 3-tert-butylcyclobutanone (1 g, 7.9 mmol) in dry tetrahydrofuran (3 mL) dropwise. Stir for 1 hour at −78° C. and then warm to room temperature over 1 hour. Slowly quench the mixture with 0.1 N hydrochloric acid. Dilute the resulting mixture with ethyl acetate and a saturated aqueous solution of sodium potassium tartrate (Rochelle salt) and stir the biphasic mixture overnight. Filter the mixture to remove precipitates and separate the aqueous layer. Saturate the aqueous phase with sodium chloride and extract with ethyl acetate. Add the organic extract to the ethyl acetate solution of the reaction mixture and wash the resultant mixture with saturated aqueous sodium chloride solution, dry (magnesium sulfate), filter, and concentrate to give the title compound as a 9:1 mixture of cis/trans diastereomers.

출처