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

HRID 570077

Reaktionsgleichung

[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

Komponenten

Reaktionsbedingungen

Temperatur: 22.5 °C

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag: ord-874d4b630d024c3a9876189974d5a211
Quelldatensatz: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09023315B2

Verknüpfte Notizen

Wird geladen…