Water → 2-Hydroxy-2-(3-nitrophenyl)ethyl acetate
Reaction equation
[C:1]([O:4][CH2:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[CH:9]=1)=[O:7])(=[O:3])[CH3:2].[BH4-].[Na+].O>CO>[C:1]([O:4][CH2:5][CH:6]([OH:7])[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[CH:9]=1)(=[O:3])[CH3:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
2-(3-Nitrophenyl)-2-oxoethyl acetate (20 g) was dissolved in MeOH (200 mL) and cooled to 0° C. Sodium borohydride (6.78 g) was added pinch-wise to the reaction mixture and this was stirred for 2 hours at room temperature. The reaction was quenched by addition of acetone (10 mL) and the mixture concentrated to give a solid. The solid was treated with water (100 mL) and extracted with ethyl acetate (3×100 mL). The crude title compound obtained was used for next step without further purification (18 g, 89%).
Workup
- customThe reaction was quenched by addition of acetone (10 mL)
- concentrationthe mixture concentrated
- customto give a solid
- extractionextracted with ethyl acetate (3×100 mL)
Sources & evidence
- ORD record
- ord-be2535aab1744d37b97bf980f8ae65cd
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08207167B2
Reaction notes
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