Dimethyl 1-trityl-3,5-pyrazoledicarboxylate → 1-Trityl-3,5-bis(hydroxymethyl)pyrazole

HRID 386348

Reaction equation

[C:1]([N:20]1[C:24]([C:25](OC)=[O:26])=[CH:23][C:22]([C:29](OC)=[O:30])=[N:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1.CCOCC>[C:1]([N:20]1[C:24]([CH2:25][OH:26])=[CH:23][C:22]([CH2:29][OH:30])=[N:21]1)([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 22.5 °C

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).

Workup

customAfter this time, the reaction was quenched by the slow addition of 1 mL of distilled water
additionfollowed by addition of 1 mL of 10% NaOH and 2.4 mL of water
customThe solids formed
customwere removed by filtration, and 50 mL of dichloromethane
additionwas added to the filtrate
customThe organic phase was separated
washwashed with distilled water
customa white microcrystalline solid was obtained
customafter evaporation of the solvent under vacuum

Sources & evidence

ORD record: ord-289c35bd6a904647ac68e4a575b46df0
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08372379B2

Linked notes

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