반응 #1771994

반응 방정식

1-methyl-1-hydroxycarbonylcyclohexane

diborane

→

1-methyl-1-hydroxymethylcyclohexane

수율 69.0%

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   기타The cooling bath was removed
2. 2
   기타The remaining borane was quenched by the slow addition of saturated sodium bisulfate (10 mL) over 90 min
3. 3
   온도with cooling
4. 4
   workup.ADDITIONAdditional saturated sodium bisulfate (200 mL) was added and after 20 min
5. 5
   workup.STIRRINGof stirring the aqueous layer
6. 6
   기타was removed
7. 7
   세척The organic layer was washed with water and saturated sodium chloride
8. 8
   기타dried
9. 9
   여과filtered
10. 10
    농축concentrated
11. 11
    기타The residue was purified by flash chromatography

실험 절차

To a solution of 1-methyl-1-hydroxycarbonylcyclohexane (10 g, 70 mmol) in tetrahydrofuran(300 mL) at 0° C. was added 1M diborane in tetrahydrofuran (200 mL, 200 mmol) over 90 minutes. The cooling bath was removed and the reaction mixture was stirred at room temperature for two days. The remaining borane was quenched by the slow addition of saturated sodium bisulfate (10 mL) over 90 min with cooling. Additional saturated sodium bisulfate (200 mL) was added and after 20 min of stirring the aqueous layer was removed. The organic layer was washed with water and saturated sodium chloride, dried, filtered and concentrated. The residue was purified by flash chromatography using 20% diethylether in hexanes to give 1-methyl-1-hydroxymethylcyclohexane (6.17 g, 48 mmol, 69%).

출처