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

HRID 928381Notes

Reaction equation

HRID 928381 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

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

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-486c5ab2a8c54811b66f349292178b26
Source dataset
uspto-grants-2016_03
Patent number
US09290485B2

Reaction notes

Loading…