Acetone → HCID 22716743, compound
Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][N:3]=1.C([Li])CCC.CCCCCC.[CH3:20][C:21]([CH3:23])=[O:22].[CH3:24][S:25][C:26]1[CH:33]=[CH:32][C:29]([CH:30]=[O:31])=[CH:28][CH:27]=1>CCOCC>[OH:22][C:21]([C:5]1[CH:6]=[CH:7][C:2]([CH:30]([C:29]2[CH:32]=[CH:33][C:26]([S:25][CH3:24])=[CH:27][CH:28]=2)[OH:31])=[N:3][CH:4]=1)([CH3:23])[CH3:20]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a suspension of 2,5-dibromopyridine (5.12 g, 1 eq) in ether at −78° C., was added n-butyllithium in hexane (1.05 eq) slowly. The resulting yellow-orange precipitate was strirred 30 min. Then acetone (1.54 ml, 1.05 eq) was added. The solution was kept at −78° C. for another 30 min. n-Butyllithium in hexane (1.1 eq) was slowly syringed to the resulting orange suspension. The suspension was then stirred 1 h at −78° C. Following this, 4-(methylthio)benzaldehyde (2.85 ml, 1.1 eq.) was added. The resulting suspension was warmed to −35° C. and quenched with a solution of NH4Cl (sat.). Water and EtOAc were added and the organic layer dried over MgSO4, evaporated and purified by flash chromatography (EtOAc) to give [5-(1-Hydroxy-1-methylethyl)-2-pyridinyl][4-(methylthio)phenyl]methanol.
Workup
- waitThe solution was kept at −78° C. for another 30 min.
- additionwas added
- temperatureThe resulting suspension was warmed to −35° C.
- customquenched with a solution of NH4Cl (sat.)
- additionWater and EtOAc were added
- dry with materialthe organic layer dried over MgSO4
- customevaporated
- custompurified by flash chromatography (EtOAc)
Sources & evidence
- ORD record
- ord-3a7b8ec81ef44513a746384d3e85f8b9
- Source dataset
- uspto-grants-2002_06
- Patent number
- US06410563B1
Reaction notes
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