Water → HCID 19600931, compound

HRID 609877Notes

Reaction equation

HRID 609877 reaction equation
[CH3:1][C:2]1([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH2:17][CH3:18])[CH:9]=2)[O:6][C:5](=[O:7])[NH:4][CH2:3]1.[H-].[Na+].Br[CH2:22][CH:23]1[CH2:25][CH2:24]1.O>CN(C)C=O>[CH3:1][C:2]1([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH2:17][CH3:18])[CH:9]=2)[O:6][C:5](=[O:7])[N:4]([CH2:22][CH:23]2[CH2:25][CH2:24]2)[CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 19358526HCID 19358526, compound

Product 1

HCID 19600931HCID 19600931, compoundYield 71.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

500 mg (2.0 mmol) of 5-methyl-5-(3-ethoxy-4-methoxyphenyl)-2-oxazolidinone was first stirred with 60 mg (2.5 mmol) of sodium hydride in 14 ml of dimethylformamide for 30 minutes and, after addition of 0.26 ml (3.0 mmol) of (bromomethyl)cyclopropane for 17 hours at room temperature. The reaction mixture was combined with 50 ml of water and then extracted with ethyl acetate. The ethyl acetate phase was washed with water, dried over sodium sulfate, filtered, and concentrated (766 mg of a yellow oil). Chromatography on silica gel with methylene chloride/ether (1:1) yielded 438 mg of 5-methyl-5-(3-ethoxy-4-methoxyphenyl)-3-cyclopropylmethyl-2-oxazolidinone as an oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate phase was washed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated (766 mg of a yellow oil)

Sources & evidence

ORD record
ord-2b96733aec574ee5bb4d591736da6332
Source dataset
uspto-grants-1999_12
Patent number
US05998453

Reaction notes

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