Sodium hydride → 3-(4,4-Diethoxybutyl)-[1,3]oxazocan-2-one

HRID 2301390Notes

Reaction equation

HRID 2301390 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8](=[O:20])[NH:9][CH2:10][CH2:11][CH2:12][CH:13]([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16].[H-].[Na+]>CN(C)C=O.O.[Cl-].[Na+]>[CH2:15]([O:14][CH:13]([O:17][CH2:18][CH3:19])[CH2:12][CH2:11][CH2:10][N:9]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1=[O:20])[CH3:16]

Participants

6

Reactant 2

HCID 24758Sodium hydrideHCID 85795399(4,4-Diethoxybutyl)carbamic acid 5-chloro-pentyl ester

Product 1

HCID 219786193-(4,4-Diethoxybutyl)-[1,3]oxazocan-2-oneYield 16.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 5234Sodium ChlorideSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (4,4-diethoxybutyl)carbamic acid 5-chloro-pentyl ester (11.4 g, 44 mmole) dissolved in N,N-dimethylformamide (100 mL) was added de-oiled sodium hydride (1.01 g, 42.3 mmole). The reaction mixture was stirred for 15 hours at room temperature, and then at 70° C. for 3 hours. The mixture was diluted with water, saturated aqueous sodium chloride was added, and extracted with diethyl ether. The organic phase was washed with water, dried (magnesium sulfate), and concentrated. Purification by silica gel chromatography, gave 3-(4,4-diethoxybutyl)-[1,3]oxazocan-2-one (2.03 g) as a viscous oil.

Workup

  1. waitat 70° C. for 3 hours
  2. additionwas added
  3. extractionextracted with diethyl ether
  4. washThe organic phase was washed with water
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated
  7. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-3be9aed05c134a168ad34719c012303e
Source dataset
uspto-grants-2002_12
Patent number
US06500822B2

Reaction notes

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