Reaction #657259

Reaction equation

dimethyl 1-trityl-3,5-pyrazoledicarboxylate

LiAlH4

→

1-trityl-3,5-bis(hydroxymethyl)pyrazole

Yield 90.0%

Solvents

THF

Et2O

Conditions

Workup

1. 1
   OtherAfter this time, the reaction was quenched by the slow addition of 1 mL of distilled water
2. 2
   workup.ADDITIONfollowed by addition of 1 mL of 10% NaOH and 2.4 mL of water
3. 3
   OtherThe solids formed
4. 4
   Otherwere removed by filtration, and 50 mL of dichloromethane
5. 5
   workup.ADDITIONwas added to the filtrate
6. 6
   OtherThe organic phase was separated
7. 7
   Washwashed with distilled water
8. 8
   Othera white microcrystalline solid was obtained
9. 9
   Otherafter evaporation of the solvent under vacuum

Procedure

To a solution of dimethyl 1-trityl-3,5-pyrazoledicarboxylate (3.200 g, 7.50 mmol) in dry THF (50 mL) were added 30 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 mL of distilled water, followed by addition of 1 mL of 10% NaOH and 2.4 mL of water. The solids formed were removed by filtration, and 50 mL of dichloromethane was added to the filtrate. The organic phase was separated, washed with distilled water and a white microcrystalline solid was obtained after evaporation of the solvent under vacuum. Yield: 90% (2.843 g, 6.71 mmol).

Source