Reacción #48668

Ecuación de reacción

lithium aluminum hydride

tert-butanol

3-tert-butylcyclobutanone

hydride

→

title compound

Cis-3-tert-butylcyclobutanol

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGStir for 1 hour at −78° C.
2. 2
   OtroSlowly 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
   FiltraciónFilter the mixture
6. 6
   Otroto remove
7. 7
   Otroprecipitates
8. 8
   Otroseparate the aqueous layer
9. 9
   ConcentraciónSaturate the aqueous phase with sodium chloride
10. 10
    Extracciónextract with ethyl acetate
11. 11
    workup.ADDITIONAdd the
12. 12
    Extracciónorganic extract to the ethyl acetate solution of the reaction mixture
13. 13
    Lavadowash the resultant mixture with saturated aqueous sodium chloride solution
14. 14
    Secadodry (magnesium sulfate)
15. 15
    Filtraciónfilter
16. 16
    Concentraciónconcentrate

Procedimiento

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.

Fuente