Reaction #1771994

Reaction equation

1-methyl-1-hydroxycarbonylcyclohexane

diborane

→

1-methyl-1-hydroxymethylcyclohexane

Yield 69.0%

Solvents

tetrahydrofuran

tetrahydrofuran

Conditions

Workup

1. 1
   OtherThe cooling bath was removed
2. 2
   OtherThe remaining borane was quenched by the slow addition of saturated sodium bisulfate (10 mL) over 90 min
3. 3
   Temperaturewith 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
   Otherwas removed
7. 7
   WashThe organic layer was washed with water and saturated sodium chloride
8. 8
   Otherdried
9. 9
   Filtrationfiltered
10. 10
    Concentrationconcentrated
11. 11
    OtherThe residue was purified by flash chromatography

Procedure

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%).

Source