Hexane → (3-ethoxy-4-methoxy-phenyl)-(1-methyl-1H-benzotriazol-5-yl)-methanol
Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([O:10][CH2:11][CH3:12])[CH:3]=1.C([Li])CCC.CCCCCC.[CH3:24][N:25]1[C:29]2[CH:30]=[CH:31][C:32]([CH:34]=[O:35])=[CH:33][C:28]=2[N:27]=[N:26]1>C1COCC1.O.C(O)(C)C>[CH2:11]([O:10][C:4]1[CH:3]=[C:2]([CH:34]([C:32]2[CH:31]=[CH:30][C:29]3[N:25]([CH3:24])[N:26]=[N:27][C:28]=3[CH:33]=2)[OH:35])[CH:7]=[CH:6][C:5]=1[O:8][CH3:9])[CH3:12]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
To a solution of 4-bromo-2-ethoxy-1-methoxy-benzene (1.5 g, 6.5 mmol) in THF (15 mL) was added a solution of n-butyllitium in hexane (2.5 mL, 2.5 N, 6.3 mmol) at −78° C. and kept for 20 min. To the mixture was added a slurry of 1-methyl-1H-benzotriazole-5-carbaldehyde (1.0 g, 6.0 mmol) in THF (5 mL) at −78° C. After 18 h, isopropanol (2 mL) and water (10 mL) was added to the mixture, and the cold bath was removed. The mixture was stirred at room temperature for 20 min. The mixture was extracted with ethyl acetate (50 mL) and water (50 mL). The aqueous layer was extracted with ethyl acetate (50 mL). The combined organic layers was washed with water (50 mL), brine (50 mL) and dried over MgSO4. Removal of solvent gave (3-ethoxy-4-methoxy-phenyl)-(1-methyl-1H-benzotriazol-5-yl)-methanol as an oil (2 g). The oil was used in the next step without further purification.
Workup
- waitAfter 18 h
- customthe cold bath was removed
- extractionThe mixture was extracted with ethyl acetate (50 mL) and water (50 mL)
- extractionThe aqueous layer was extracted with ethyl acetate (50 mL)
- washThe combined organic layers was washed with water (50 mL), brine (50 mL)
- dry with materialdried over MgSO4
- customRemoval of solvent
Sources & evidence
- ORD record
- ord-8aec90f965a646ae91c6322b0303dde2
- Source dataset
- uspto-grants-2008_12
- Patent number
- US07468446B2
Reaction notes
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