Cyclohexanol → HCID 11962050, compound

HRID 1865097Notes

Reaction equation

F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH:11]1([OH:17])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>>[CH:11]1([O:17][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

Reactant 2

HCID 7966Cyclohexanol

HCID 9590p-Fluoronitrobenzene

Product 1

HCID 11962050HCID 11962050, compound

Procedure

Prepare the title compound in the manner analogous to the procedure set fourth in example E-227 using 4-fluoro-nitrobenzene and cyclohexanol (heat 1.5 hours at 55° C.). Purify the material by silica gel chromatography (Prep.2000) eluting with methylene chloride/hexane 1:1 to provide the title compound as an oil. Mass spectrum (m/e): 221.1 (M*). (Bruker 300) 1H NMR (CDCl3) δ 8.13-8.18 (2H, d), 6.90-6.93 (2H, d), 4.31-4.39 (1H, m), 1.92-2.02 (2H, m), 1.75-1.85 (2H, m), 1.50-1.62 (3H, m), 1.28-1.44 (3H, m).

Workup

customPurify the material by silica gel chromatography (Prep.2000)
washeluting with methylene chloride/hexane 1:1

Sources & evidence

ORD record: ord-012ed34077264fdc8647b29140c3e4d9
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625932B2

Reaction notes

Loading…