Water → HCID 22618881, compound

HRID 842275Notes

Reaction equation

HRID 842275 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][C:12]1([CH3:18])[CH2:16][O:15][C:14](=[O:17])[NH:13]1.[CH2:19](Br)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].O>CN(C)C=O.O1CCCC1>[CH2:19]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][C:12]1([CH3:18])[CH2:16][O:15][C:14](=[O:17])[NH:13]1)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

7

Reactant 4

HCID 962WaterHCID 123691-BromoheptaneHCID 24758Sodium hydrideHCID 22618819HCID 22618819, compound

Product 1

HCID 22618881HCID 22618881, compoundYield 83.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of sodium hydride (90 mg) in dimethylformamide (1 ml), under ice-cooling, a solution of 4-(2-(2-hydroxyphenyl)ethyl)-4-methyl-2-oxazolidinone (0.50 g) in dimethylformamide (2 ml) was added and the mixture was stirred at room temperature for 2 hours. To the solution, a solution of heptyl bromide (0.47 g) in tetrahydrofuran (2 ml) was added and the mixture was stirred at the same temperature for 5.5 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with a saturated brine and dried over magnesium sulfate. The solvent was distilled away under reduced pressure and the residue was subjected to silica gel chromatography (eluent; hexane ethyl acetate=1:1) to give the subject compound (0.60 g).

Workup

  1. temperatureunder ice-cooling
  2. stirringthe mixture was stirred at the same temperature for 5.5 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with a saturated brine
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-c35e593f54954e718f0b0fbcd6726412
Source dataset
uspto-grants-2002_04
Patent number
US06372800B1

Reaction notes

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