Methyl iodide → HCID 53814232, compound

HRID 846240Notes

Reaction equation

HRID 846240 reaction equation
[CH3:1][N:2]([CH3:20])[C:3]([S:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:19])[CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:8][CH:7]=1)=[O:4].[H-].[K+].[CH3:23]I>C1COCC1.CCOCC>[CH3:20][N:2]([CH3:1])[C:3]([S:5][C:6]1[CH:7]=[CH:8][C:9]([C:12](=[O:19])[CH:13]([CH3:23])[CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:10][CH:11]=1)=[O:4]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 82127Potassium hydrideHCID 14211171HCID 14211171, compound

Product 1

HCID 53814232HCID 53814232, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-45 °C

Procedure

The compound from Step D, (10.0 g, 33.9 mmoles) was dissolved in THF (100 ml) and added dropwise to a stirred mixture of potassium hydride (1.6 g, 40.7 mmoles) in THF (10 ml) at -45° C. The reaction mixture was warmed to 0° to initiate the reaction, then cooled to -45° C. After 30 minutes, the reaction mixture was warmed to 0° C., and stirred for 10 minutes A solution of methyl iodide (3.17 ml, 50.9 mmoles) in THF (10 ml) was added slowly to the cold solution. The mixture was stirred at 0° for one hour. The reaction mixture was diluted with ether, washed with water, brine, dried and evaporated to yield an oil which was purified by HPLC to yield the title compound.

Workup

  1. temperatureThe reaction mixture was warmed to 0°
  2. customthe reaction
  3. temperaturethe reaction mixture was warmed to 0° C.
  4. additionwas added slowly to the cold solution
  5. washwashed with water, brine
  6. customdried
  7. customevaporated
  8. customto yield an oil which
  9. customwas purified by HPLC

Sources & evidence

ORD record
ord-d771b9d464154ed89d9ca193c7e23461
Source dataset
uspto-grants-1992_08
Patent number
US05135940

Reaction notes

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