Cyclohexene oxide → (1S*,2R*)-2-(1-Ethyl-1H-pyrazol-5-yl)cyclohexanol

HRID 337723Notes

Reaction equation

HRID 337723 reaction equation
[CH2:1]([N:3]1[CH:7]=[CH:6][CH:5]=[N:4]1)[CH3:2].C([Li])CCC.[CH:13]12[O:19][CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18]2>C1COCC1>[CH2:1]([N:3]1[C:7]([C@H:13]2[CH2:18][CH2:17][CH2:16][CH2:15][C@@H:14]2[OH:19])=[CH:6][CH:5]=[N:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 9246Cyclohexene oxideHCID 4984461-EthylpyrazoleHCID 178418339Butyllithium

Product 1

HCID 89962898(1S*,2R*)-2-(1-Ethyl-1H-pyrazol-5-yl)cyclohexanolYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The reaction and aftertreatment were conducted in the same manner as in Example 4a by using 1-ethylpyrazole (2.50 g, 26.0 mmol), butyl lithium (1.63 M solution in hexane; 18.1 mL, 29.5 mmol), cyclohexene oxide (2.97 g, 30.3 mmol) and THF (60 mL), to yield the title compound (2.86 g, 57%) as a colorless oil.

Workup

  1. customThe reaction and aftertreatment

Sources & evidence

ORD record
ord-d8668b72b9874a869aa94e5db16b42b7
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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