Sodium borohydride → 2-Butyl-5-nitro-2,3-dihydrobenzofuran-3-ol
Reaction equation
[CH2:1]([CH:5]1[C:9](=[O:10])[C:8]2[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:7]=2[O:6]1)[CH2:2][CH2:3][CH3:4].[BH4-].[Na+]>C(O)C.O>[CH2:1]([CH:5]1[CH:9]([OH:10])[C:8]2[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:7]=2[O:6]1)[CH2:2][CH2:3][CH3:4]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
700 mg of 2-(n-butyl)-5-nitro-3(2H)-benzofuranone were introduced into 10 ml of ethanol in a 50 ml flask and cooled to 0° C. A solution of 130 mg of NaBH4 in 5 ml of ethanol was added dropwise thereto, an intense red coloration immediately appearing. The mixture was allowed to reach room temperature and was then briefly heated to reflux. After cooling to room temperature, the reaction mixture was taken up in water and dichloromethane, the organic phase was separated off, and the aqueous phase was extracted once more with dichloromethane. Drying of the combined organic phases over sodium sulphate, removal of the solvent in vacuo and column chromatography (eluent: hexane:ethyl acetate=5:1) resulted in 400 mg (57% of theory) of 2-(n-butyl)-5-nitro-2,3-dihydrobenzofuran-3-ol.
Workup
- customto reach room temperature
- temperaturewas then briefly heated to reflux
- temperatureAfter cooling to room temperature
- customdichloromethane, the organic phase was separated off
- extractionthe aqueous phase was extracted once more with dichloromethane
- dry with materialDrying of the combined organic phases over sodium sulphate, removal of the solvent in vacuo and column chromatography (eluent: hexane:ethyl acetate=5:1)
- customresulted in 400 mg (57% of theory) of 2-(n-butyl)-5-nitro-2,3-dihydrobenzofuran-3-ol
Sources & evidence
- ORD record
- ord-94d392b3e58140f7ac2634e0cf3cd33f
- Source dataset
- uspto-grants-2006_01
- Patent number
- US06984741B2
Reaction notes
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