Tetrahydrofuran → HCID 89962282, compound

Reaction equation

I[C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.[CH2:7]([Li])[CH2:8][CH2:9][CH3:10].[CH2:12]1[CH2:16][O:15][CH2:14][CH2:13]1>>[CH:14]12[O:15][CH:16]1[CH2:12][CH2:2][CH2:6][CH2:13]2.[NH:4]1[CH:3]=[C:8]([C@@H:9]2[CH2:10][CH2:16][CH2:12][CH2:13][C@H:14]2[OH:15])[CH:7]=[N:5]1

Participants

Reactant 3

HCID 8028Tetrahydrofuran

HCID 770224-Iodopyrazole

HCID 178418339Butyllithium

Product 2

HCID 9246Cyclohexene oxide

HCID 89962282HCID 89962282, compoundYield 10%

Procedure

The reaction and aftertreatment were conducted in the same manner as in Example 155b by using 4-iodo-1H-pyrazole (5.82 g, 30.0 mmol), butyl lithium (2.69 M solution in hexane; 22.3 mL, 60.0 mmol), a boron trifluoride-diethyl ether complex (7.54 mL, 60.0 mmol), cyclohexene oxide (3.24 g, 33.0 mmol) and THF (120 mL), to yield the title compound (0.48 g, 10%) as a colorless solid.