Methyl iodide → HCID 19600924, compound

HRID 1957182Notes

Reaction equation

HRID 1957182 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][CH:18]3[CH2:20][CH2:19]3)[CH:9]=2)[O:6][C:5](=[O:7])[NH:4][CH2:3]1.[OH-].[K+].[CH3:23]I>O1CCCC1>[CH:18]1([CH2:17][O:16][C:10]2[CH:9]=[C:8]([C:2]3([CH3:1])[O:6][C:5](=[O:7])[N:4]([CH3:23])[CH2:3]3)[CH:13]=[CH:12][C:11]=2[O:14][CH3:15])[CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 13653220HCID 13653220, compound

Product 1

HCID 19600924HCID 19600924, compoundYield 40.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

500 mg (1.8 mmol) of 5-methyl-5-(3-cyclopropylmethoxy-4-methoxyphenyl)-2-oxazolidinone, 113 mg (2.0 mmol) of potassium hydroxide, and 0.15 ml (2.2 mmol) of methyl iodide were stirred in 4 ml of tetrahydrofuran for 4 hours at room temperature. The reaction mixture was filtered, the filtrate combined with 30 ml of water and then extracted with ethyl acetate. The ethyl acetate phase was washed with water, dried over sodium sulfate, filtered, and concentrated (390 mg of a yellow oil). By PSC separation with methylene chloride/ether (1:1), 212 mg of 5-(3-cyclopropylmethoxy-4-methoxyphenyl)-3,5-dimethyl2-oxazolidinone was obtained as an oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate phase was washed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated (390 mg of a yellow oil)
  7. customBy PSC separation with methylene chloride/ether (1:1)

Sources & evidence

ORD record
ord-12fc25b718d640d888339887b8fd31d9
Source dataset
uspto-grants-1998_07
Patent number
US05783591

Reaction notes

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