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

HRID 479353Notes

Reaction equation

HRID 479353 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-d0a40682bc7e49ec90253f426ee49fcd
Source dataset
uspto-grants-2003_11
Patent number
US06645958B2

Reaction notes

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