Tetrahydrofuran → HCID 89962682, compound

HRID 337994Notes

Reaction equation

HRID 337994 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][N:7]1[CH:11]=[CH:10][CH:9]=[N:8]1.[CH2:12]([Li])[CH2:13][CH2:14]C.[CH2:17]1[CH2:21][O:20][CH2:19][CH2:18]1>>[CH:4]12[O:5][CH:6]1[CH2:12][CH2:13][CH2:14][CH2:3]2.[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][N:7]1[C:11]([C@H:17]2[CH2:18][CH2:19][CH2:13][CH2:12][C@@H:21]2[OH:20])=[CH:10][CH:9]=[N:8]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 89963172HCID 89963172, compoundHCID 178418339Butyllithium

Product 2

HCID 9246Cyclohexene oxideHCID 89962682HCID 89962682, compoundYield 60%

Procedure

The reaction and aftertreatment were conducted in the same manner as in Example 155b by using the 1-[(2-methoxyethoxy)methyl]-1H-pyrazole (2.00 g, 12.8 mmol) prepared in Example 155a, butyl lithium (2.69 M solution in hexane; 4.76 mL, 12.8 mmol), a boron trifluoride-diethyl ether complex (2.68 mL, 21.3 mmol), cyclohexene oxide (1.05 g, 10.7 mmol) and THF (100 mL), to yield the title compound (1.64 g, 60%) as a colorless oil.

Workup

  1. customThe reaction and aftertreatment

Sources & evidence

ORD record
ord-0338560ea84b4bdca1063e1bc5d90e7c
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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