Reaction #657261

Reaction equation

trimethyl 1-trityl-3,4,5-pyrazoletricarboxylate

LiAlH4

→

1-trityl-3,4,5-tris(hydroxymethyl)pyrazole

Yield 73.0%

Solvents

THF

Et2O

Conditions

Workup

1. 1
   OtherAfter this time, the reaction was quenched by the slow addition of 1.5 mL of distilled water
2. 2
   workup.ADDITIONfollowed by addition of 1.5 mL of 10% NaOH and 3.5 mL of water
3. 3
   OtherThe solids formed
4. 4
   Otherwere removed by filtration, and 80 mL of dichloromethane
5. 5
   workup.ADDITIONwas added to the filtrate
6. 6
   OtherThe organic phase was separated
7. 7
   Washwashed with distilled water (70 mL)
8. 8
   Otherafter separation from the aqueous phase
9. 9
   Dryingwas dried over MgSO4
10. 10
    OtherAfter separation of the organic phase
11. 11
    Otherthe solvent was evaporated under vacuum
12. 12
    Otheryielding a yellowish solid

Procedure

To a solution of trimethyl 1-trityl-3,4,5-pyrazoletricarboxylate (3.034 g, 6.26 mmol) in dry THF (60 mL) were added 50 mL of 1.0 M LiAlH4 in Et2O. The resulting solution was stirred for about 16 h at room temperature (20-25° C.). After this time, the reaction was quenched by the slow addition of 1.5 mL of distilled water, followed by addition of 1.5 mL of 10% NaOH and 3.5 mL of water. The solids formed were removed by filtration, and 80 mL of dichloromethane was added to the filtrate. The organic phase was separated, washed with distilled water (70 mL) and, after separation from the aqueous phase, was dried over MgSO4. After separation of the organic phase, the solvent was evaporated under vacuum yielding a yellowish solid. Yield: 73% (1.823 g, 4.54 mmol).

Source