Water → 1-Cyano-1-[3-[4-(2-methylimidazol-1-yl)benzyloxy]phenyl]-cyclobutane

HRID 1108090Notes

Reaction equation

[C:1]([C:3]1([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([OH:13])[CH:8]=2)[CH2:6][CH2:5][CH2:4]1)#[N:2].Cl.[CH3:15][C:16]1[N:17]([C:21]2[CH:28]=[CH:27][C:24]([CH2:25]Cl)=[CH:23][CH:22]=2)[CH:18]=[CH:19][N:20]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[C:1]([C:3]1([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:25][C:24]3[CH:23]=[CH:22][C:21]([N:17]4[CH:18]=[CH:19][N:20]=[C:16]4[CH3:15])=[CH:28][CH:27]=3)[CH:8]=2)[CH2:6][CH2:5][CH2:4]1)#[N:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 1-cyano-1-(3-hydroxyphenyl)cyclobutane (1.76 g, 10 mmol), 4-(2-methylimidazol-1-yl)benzylchloride hydrochloride (2.10 g, 10 mmol) and potassium carbonate (6.90 g, 50 mmol) in DMF (80 ml) were stirred together at 80° C. for 3 hrs. Water (200 ml) was added and the mixture extracted with ethyl acetate/benzene (2/1, 100 ml×2), washed with water (100 ml×2), brine (100 ml), dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography (SiO2, 150 g; dichloromethane/methanol (20/1)) to afford 2.90 g (84%) of the titled compound as a clear yellow oil.

Workup

extractionthe mixture extracted with ethyl acetate/benzene (2/1, 100 ml×2)
washwashed with water (100 ml×2), brine (100 ml)
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography (SiO2, 150 g; dichloromethane/methanol (20/1))

Sources & evidence

ORD record: ord-ecf95db6dddd4e11b827ef36388c6098
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06063928

Reaction notes

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