Hydrochloric Acid → HCID 66773781, compound

HRID 1985898Notes

Reaction equation

C(OC(OCC)[N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1)C.C([Li])CCC.[CH3:18][C:19]1[CH:20]=[C:21]([C:25](=[O:27])[CH3:26])[CH:22]=[CH:23][CH:24]=1.Cl.C(=O)([O-])O.[Na+]>O1CCCC1>[NH:7]1[CH:8]=[CH:9][N:5]=[C:6]1[C:25]([C:21]1[CH:22]=[CH:23][CH:24]=[C:19]([CH3:18])[CH:20]=1)([OH:27])[CH3:26]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1-(diethoxymethyl)-1H-imidazole (935 mg, 5.5 mmol) in anhydrous tetrahydrofuran (6 ml), at −78° C., was added n-butyllithium (2.5M in hexanes, 2.2 ml, 5.5 mmol). The mixture was allowed to warm to 0° C. and then added to a solution of 1-(3-methylphenyl)ethanone (670 mg, 5.0 mmol) in anhydrous tetrahydrofuran (5 ml), also at 0° C. The reaction mixture was stirred at 0° C. for 30 min and then at room temperature for 1 h. The mixture was poured into cold hydrochloric acid (4N, 10 ml) and stirred for 20 min. The mixture was adjusted to pH 7 by addition of sodium hydrogen carbonate and then extracted with dichloromethane. The combined extracts were dried (MgSO4) and concentrated in vacuo to give the title compound (850 mg).

Workup

waitat room temperature for 1 h
stirringstirred for 20 min
extractionextracted with dichloromethane
dry with materialThe combined extracts were dried (MgSO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-773ba4d1f09e499dae7da85178e09326
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07547718B2

Reaction notes

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