Sodium borohydride → 3-(2-Hydroxyethoxy)benzonitrile
Reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([O:9][CH2:10][C:11](OCC)=[O:12])[CH:6]=[CH:7][CH:8]=1)#[N:2].[BH4-].[Na+]>C(O)C>[OH:12][CH2:11][CH2:10][O:9][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[C:1]#[N:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
A suspension of ethyl [(3-cyanophenyl)oxy]acetate obtained in Reference Example 29 (8.00 g, 39.0 mmol) and sodium borohydride (1.47 g, 39.0 mmol) in ethanol (120 mL) was stirred at 50° C. for 15 hr, and the mixture was concentrated under reduced pressure. The residue was extracted with ethyl acetate and water, and the organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated to give the title compound as a white powder (5.85 g, 92%).
Workup
- concentrationthe mixture was concentrated under reduced pressure
- extractionThe residue was extracted with ethyl acetate and water
- washthe organic layer was washed with saturated brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-a21f18d2203143ca96e35a5397f7c9bf
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07915267B2
Reaction notes
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