2-Nitropropane → 2-Methyl-1-(naphthalen-2-YL)-2-nitropropan-1-OL
Reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[N+:19]([CH:22]([CH3:24])[CH3:23])([O-:21])=[O:20].[CH:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][C:26]=1[CH:35]=[O:36].C([Si](C)(C)Cl)(C)(C)C>O1CCCC1.C(N(CC)CC)C>[CH3:23][C:22]([N+:19]([O-:21])=[O:20])([CH3:24])[CH:35]([C:26]1[CH:27]=[CH:28][C:29]2[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:25]=1)[OH:36]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To tetrabutylammonium fluoride 3 hydrate (2.41 g) was added tetrahydrofuran (20 ml) and the mixture was ice-cooled. To the mixture were added 2-nitropropane (2.7 ml), 2-naphthaldehyde (3.12 g) and triethylamine (2.8 ml) under an argon atmosphere. To the mixture was added a solution of tert-butyldimethylchlorosilane (4.51 g) in tetrahydrofuran (20 ml). The resulting mixture was stirred for 40 min while allowing to warm to room temperature from ice-cooling. After removing insoluble matter by filtration, the filtrate was poured into a solution (500 ml) of diethyl ether-n-hexane=1:3 and the mixture was washed twice with water (40 ml). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was subjected to crystallization from n-hexane to give the title compound (3.78 g).
Workup
- temperaturecooled
- temperaturecooling
- customAfter removing insoluble matter
- filtrationby filtration
- additionthe filtrate was poured into a solution (500 ml) of diethyl ether-n-hexane=1:3
- washthe mixture was washed twice with water (40 ml)
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe obtained residue was subjected to crystallization from n-hexane
Sources & evidence
- ORD record
- ord-2f2e9ac4566b444c9eb2e1c7e48b1980
- Source dataset
- uspto-grants-2005_07
- Patent number
- US06916956B2
Reaction notes
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