Hydrochloric Acid → HCID 23154708, compound
Reaction equation
[CH3:1][CH:2]([C:4](=[O:16])[CH:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-:15])=[O:14])[CH3:6])[CH3:3].[BH4-].[Na+].Cl>CO>[CH3:3][CH:2]([CH:4]([OH:16])[CH:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-:15])=[O:14])[CH3:6])[CH3:1]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
In a 25 ml flask was prepared a solution of 2-methyl-4-(2-nitro-phenyl)-pentan-3-one (390 mg, 1.8 mmol) in dry methanol (9 ml). It is cooled with an ice-water bath. The temperature in the reaction mixture was 4° C. Sodium borohydride (73 mg, 1.9 mmol) was added, spoon by spoon. It was stirred one hour at 0° C. The cooled mixture was added to HCl 1N (7 ml). This addition was exothermic. Methanol was evaporated. The aqueous phase was extracted with ethyl acetate (50 ml). The organic phase was washed with water (1×25 ml), brine (1×25 ml) and dried with magnesium sulfate. 2-methyl-4-(2-nitro-phenyl)-pentan-3-ol (380 mg—yield 97%) was then obtained as a pale yellow oil.
Workup
- temperatureIt is cooled with an ice-water bath
- customwas 4° C
- additionThis addition
- customMethanol was evaporated
- extractionThe aqueous phase was extracted with ethyl acetate (50 ml)
- washThe organic phase was washed with water (1×25 ml), brine (1×25 ml)
- dry with materialdried with magnesium sulfate
Sources & evidence
- ORD record
- ord-2632e14ede334981899f6b92dcd6bd46
- Source dataset
- uspto-grants-2011_01
- Patent number
- US07872146B2
Reaction notes
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