Ethyl 3-oxohexanoate → HCID 178450613, compound
Reaction equation
[N:1]([O-:3])=O.[Na+].[O:5]=[C:6]([CH2:13][CH2:14][CH3:15])[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9]>O.C(O)(=O)C>[OH:3][N:1]=[C:7]([C:6](=[O:5])[CH2:13][CH2:14][CH3:15])[C:8]([O:10][CH2:11][CH3:12])=[O:9]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 20 °C
Procedure
A solution of sodium nitrite (2.94) in water (7 ml) was added over 1.5 h at 25°-30° C. to a stirred solution of ethyl 3-oxohexanoate (5.0 g) in glacial acetic acid (6 ml). The orange mixture was stirred at 25° C. for 0.5 h before dilution with water (2 ml) and stirring at 20° C. for 15.5 h. The mixture was extracted with ether (2×20 ml) and the combined extracts washed with water (20 ml), 8% sodium bicarbonate (2×20 ml) and saturated sodium chloride solution (20 ml). The yellow solution was then dried and evaporated in vacuo, to afford a mobile yellow oil (4.95 g).
Workup
- extractionThe mixture was extracted with ether (2×20 ml)
- washthe combined extracts washed with water (20 ml), 8% sodium bicarbonate (2×20 ml) and saturated sodium chloride solution (20 ml)
- customThe yellow solution was then dried
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-719d200b98df4d818089e9fb8ad70c9c
- Source dataset
- uspto-grants-1994_12
- Patent number
- US05374646
Reaction notes
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