3-(4,4-Diethoxybutyl)-[1,3]oxazocan-2-one → 4-(2-Oxo-[1,3]oxazocan-3-yl)-butyraldehyde

HRID 2415221Notes

Reaction equation

HRID 2415221 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]1

Participants

3

Reactant 1

HCID 219786193-(4,4-Diethoxybutyl)-[1,3]oxazocan-2-one

Product 1

HCID 219786134-(2-Oxo-[1,3]oxazocan-3-yl)-butyraldehydeYield 99.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. dissolutiondissolved in dichloromethane
  6. dry with materialThe solution was dried with magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-bf539f624e9c4460bdd0ca6190d25d01
Source dataset
uspto-grants-2004_11
Patent number
US06818645B2

Reaction notes

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