Imidazole → HCID 22718710, compound

HRID 1582627Notes

Reaction equation

[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.CC(C)([O-])C.[K+].[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=1[C:27]1([CH3:30])[CH2:29][O:28]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C)C=O>[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=1[C:27]([OH:28])([CH3:29])[CH2:30][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Imidazole (4.0 g, 58.8 mmol) and potassium t-butoxide (6.5 g, 57.9 mmol) were added to a solution of 2-(2-(benzyloxy)-5-chlorophenyl)-2-methyloxirane [compound (10-1), obtained in Referential Example 8] (4.4 g) in dimethylformamide (60 mL), and the mixture was stirred for 12 hours at 80° C. After the mixture was cooled to room temperature, ice-water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with water and dried over magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified through silica gel column chromatography and dried under reduced pressure, to thereby yield 2-(2-(benzyloxy)-5-chlorophenyl)-1-(1H-1-imidazolyl)-2-propanol as colorless crystals (5.0 g, yield: 75.8%).

Workup

temperatureAfter the mixture was cooled to room temperature
extractionfollowed by extraction with ethyl acetate
washThe organic layer was washed with water
dry with materialdried over magnesium sulfate
customThe solvent was removed under reduced pressure
customThe residue was purified through silica gel column chromatography
customdried under reduced pressure

Sources & evidence

ORD record: ord-6a79a927cf9a4b44a9590f67bedea9f9
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06737434B2

Reaction notes

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