3-(4,4-Diethoxybutyl)-[1,3]oxazocan-2-one → 4-(2-Oxo-[1,3]oxazocan-3-yl)-butyraldehyde
Reaction equation
C([O:3][CH:4](OCC)[CH2:5][CH2:6][CH2:7][N:8]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][O:10][C:9]1=[O:16])C>O1CCCC1>[O:16]=[C:9]1[N:8]([CH2:7][CH2:6][CH2:5][CH:4]=[O:3])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][O:10]1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 3-(4,4-diethoxybutyl)-[1,3]oxazocan-2-one (2 g, 7.3 mmole) and 1.5 g Dowex 50W2-200 ion exchange resin in 3% aqueous tetrahydrofuran (30 mL) was heated under reflux for 24 hours. The mixture was filtered, and the filtrate was concentrated and dissolved in dichloromethane. The solution was dried with magnesium sulfate and concentrated to give 4-(2-oxo-[1,3]oxazocan-3-yl)-butyraldehyde (1.45 g) as a viscous oil which solidified.
Workup
- temperaturewas heated
- temperatureunder reflux for 24 hours
- filtrationThe mixture was filtered
- concentrationthe filtrate was concentrated
- dissolutiondissolved in dichloromethane
- dry with materialThe solution was dried with magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-8668e53dc262478281808d4d95ac9c3e
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07094778B2
Reaction notes
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