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

HRID 10187Notes

Reaction equation

HRID 10187 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-8668e53dc262478281808d4d95ac9c3e
Source dataset
uspto-grants-2006_08
Patent number
US07094778B2

Reaction notes

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