Styrene Oxide → Ethyl 1-(2-hydroxy-1-phenylethyl)-1H-pyrazole-4-carboxylate

HRID 928381

Reaktionsgleichung

Reaktionsgleichung von HRID 928381
[NH:1]1[CH:5]=[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:3]=[N:2]1.[CH2:11]1[O:19][CH:12]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O.O.O.O.O.O.[N+]([O-])([O-])=O.[Y+3].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O>[OH:19][CH2:11][CH:12]([N:1]1[CH:5]=[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:3]=[N:2]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

4

Edukt 2

HCID 7276Styrene OxideHCID 142179ethyl 1H-pyrazole-4-carboxylate

Produkt 1

HCID 58081358Ethyl 1-(2-hydroxy-1-phenylethyl)-1H-pyrazole-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 166833Yttrium (III) nitrate hexahydrate (1:3:6)Katalysator

Versuchsvorschrift

A mixture of ethyl 1H-pyrazole-4-carboxylate (1.5 g, 10.7 mmol), yttrium (III) nitrate hexahydrate (82.0 mg, 0.214 mmol) and styrene oxide (1.21 ml, 10.7 mmol) was stirred at rt for 17 h, before it was adsorbed on celite. Purification by column chromatography (CombiFlash Companion, 12 g SiO2, heptane to EA) afforded the title compound. LCMS RtM=1.72 min, [M+H]+=261.2.

Aufarbeitung

  1. customPurification by column chromatography (CombiFlash Companion, 12 g SiO2, heptane to EA)

Quellen und Nachweise

ORD-Eintrag
ord-486c5ab2a8c54811b66f349292178b26
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290485B2

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