Hydrochloric Acid → (2-t-Butyl-phenyl)-(8-fluoro-quinolin-3-yl)-methanol
Reaction equation
C([Li])CCC.C([Mg]Cl)CCC.[F:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[N:21]=[CH:20][C:19](I)=[CH:18]2.[C:24]([C:28]1[CH:35]=[CH:34][CH:33]=[CH:32][C:29]=1[CH:30]=[O:31])([CH3:27])([CH3:26])[CH3:25].Cl>O1CCCC1>[C:24]([C:28]1[CH:35]=[CH:34][CH:33]=[CH:32][C:29]=1[CH:30]([C:19]1[CH:20]=[N:21][C:22]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[CH:14][C:13]=2[F:12])[OH:31])([CH3:27])([CH3:25])[CH3:26]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
After 3 ml of tetrahydrofuran was cooled to −10° C., 0.91 ml of n-butyllithium (2.6 M hexane solution) and 1.35 ml of n-butylmagnesium chloride (0.91 M tetrahydrofuran solution) were added. After 30 minutes of stirring, 0.98 g of 8-fluoro-3-iodoquinoline was added and the mixture was stirred for 15 minutes. 0.49 g of 2-t-butylbenzaldehyde was added to the reaction solution and the mixture was stirred for 3 hours. After dilute hydrochloric acid was added to the reaction mixture, the liquid was separated with ethyl acetate. After the organic layer was concentrated and purified by silica gel column chromatography, 0.55 g of (2-t-butyl-phenyl)-(8-fluoro-quinolin-3-yl)-methanol (Compound Number 54) was obtained.
Workup
- stirringthe mixture was stirred for 15 minutes
- stirringthe mixture was stirred for 3 hours
- customthe liquid was separated with ethyl acetate
- concentrationAfter the organic layer was concentrated
- custompurified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-6121e30fa300498ebc8e9c6f737901fe
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08772200B2
Reaction notes
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