反应 #48668

反应方程式

lithium aluminum hydride

tert-butanol

3-tert-butylcyclobutanone

hydride

→

title compound

Cis-3-tert-butylcyclobutanol

溶剂

tetrahydrofuran

反应条件

后处理

1. 1
   workup.STIRRINGStir for 1 hour at −78° C.
2. 2
   其他Slowly 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
   过滤Filter the mixture
6. 6
   其他to remove
7. 7
   其他precipitates
8. 8
   其他separate the aqueous layer
9. 9
   浓缩Saturate the aqueous phase with sodium chloride
10. 10
    萃取extract with ethyl acetate
11. 11
    workup.ADDITIONAdd the
12. 12
    萃取organic extract to the ethyl acetate solution of the reaction mixture
13. 13
    洗涤wash the resultant mixture with saturated aqueous sodium chloride solution
14. 14
    干燥dry (magnesium sulfate)
15. 15
    过滤filter
16. 16
    浓缩concentrate

实验过程

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.

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