Water → HCID 14836220, compound

HRID 1087759Notes

Reaction equation

HRID 1087759 reaction equation
[H-].[Na+].[OH:3][CH2:4][CH2:5][N:6]1[CH2:10][CH2:9][O:8][C:7]1=[O:11].Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].O>C1COCC1.CN(C=O)C>[CH2:13]([O:3][CH2:4][CH2:5][N:6]1[CH2:10][CH2:9][O:8][C:7]1=[O:11])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

7

Reactant 4

HCID 962WaterHCID 81401-BromooctaneHCID 24758Sodium hydrideHCID 768872-Oxazolidinone, 3-(2-hydroxyethyl)-

Product 1

HCID 14836220HCID 14836220, compoundYield 79.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 5.12 g of 60% NaH in 130 ml of THF and 30 ml of DMF was added 12.9 of 3-(2-hydroxyethyl)oxazolidin-2-one and the contents were refluxed for 2 hours. 17 g of 1-bromooctane was added and the reaction mixture was refluxed overnight. It was cooled, poured into water and extracted with ether. The combined organic extracts were dried, concentrated and the residue Was kugelrohr distilled (150°-155° C./0.5 mm) to give 16.87 g (79.6%) of an oil.

Workup

  1. temperaturethe contents were refluxed for 2 hours
  2. temperaturethe reaction mixture was refluxed overnight
  3. temperatureIt was cooled
  4. extractionextracted with ether
  5. customThe combined organic extracts were dried
  6. concentrationconcentrated
  7. distillationdistilled (150°-155° C./0.5 mm)

Sources & evidence

ORD record
ord-40c256ca58dc4a6aa22b78cb8c341802
Source dataset
uspto-grants-1990_10
Patent number
US04960771

Reaction notes

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