Cyclohexene oxide → (1S*,2R*)-2-(1-Methyl-1H-1,2,3-triazol-5-yl)cyclohexanol

HRID 337865Notes

Reaction equation

HRID 337865 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[N:3]1.C([Li])CCC.[CH:12]12[O:18][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17]2>C1COCC1>[CH3:1][N:2]1[C:6]([C@H:12]2[CH2:17][CH2:16][CH2:15][CH2:14][C@@H:13]2[OH:18])=[CH:5][N:4]=[N:3]1

Participants

5

Reactant 3

HCID 9246Cyclohexene oxideHCID 1401191-Methyl-1H-1,2,3-triazoleHCID 178418339Butyllithium

Product 1

HCID 89963212(1S*,2R*)-2-(1-Methyl-1H-1,2,3-triazol-5-yl)cyclohexanolYield 4.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The reaction and aftertreatment were conducted in the same manner as in Example 8a by using 1-methyl-1H-1,2,3-triazole (2.00 g, 24.1 mmol), n-butyl lithium (2.69 M solution in hexane; 9.0 mL, 24.2 mmol), cyclohexene oxide (2.40 g, 24.5 mmol) and THF (70 mL), to yield the title compound (197 mg, 4.5%) as a colorless oil.

Workup

  1. customThe reaction and aftertreatment

Sources & evidence

ORD record
ord-da00f302aa8b40228101691a246ef92c
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

Loading…