Methyl iodide → HCID 18961189, compound

HRID 1708152Notes

Reaction equation

HRID 1708152 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[CH2:19][N:18]([OH:20])[C:17](=[O:21])[CH2:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CI.[C:24](=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>CN1CCCC1=O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[CH2:19][N:18]([O:20][CH3:24])[C:17](=[O:21])[CH2:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 18961175HCID 18961175, compound

Product 1

HCID 18961189HCID 18961189, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture containing 0.7 g 4-(4-benzyloxyphenyl)1-hydroxy2-pyrrolidone (Example 2), 5.0 ml methyl iodide and 2.0 g potassium carbonate in 5.0 ml N-methylpyrrolidone was stirred for 2 h at 50° C. 20 ml 1N sodium hydroxide solution was then added and the solution was extracted with a mixture of 20 ml cyclohexane and 10 ml of ether. The extract was washed with water and concentrated in vacuo whereupon the product crystallized. yield 0.31 g (41%), mp 92°-97° C.

Workup

  1. extractionthe solution was extracted with a mixture of 20 ml cyclohexane and 10 ml of ether
  2. washThe extract was washed with water
  3. concentrationconcentrated in vacuo whereupon the product
  4. customcrystallized

Sources & evidence

ORD record
ord-8895a0bf7aee481080cf0441b135d383
Source dataset
uspto-grants-1994_10
Patent number
US05356923

Reaction notes

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