Methyl iodide → HCID 70389259, compound

HRID 2292315Notes

Reaction equation

HRID 2292315 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:11]([CH3:14])([CH3:13])[CH2:10][CH2:9][C:8]([CH3:16])([CH3:15])[C:7]=2[CH:6]=[C:5]([O:17][CH3:18])[C:4]=1/[CH:19]=[CH:20]/[C:21]1[CH:28]=[CH:27][C:24]([CH2:25][OH:26])=[CH:23][CH:22]=1.[H-].[Na+].[H][H].I[CH3:34]>CN(C)C=O.CO.O>[CH3:34][O:26][CH2:25][C:24]1[CH:23]=[CH:22][C:21](/[CH:20]=[CH:19]/[C:4]2[C:5]([O:17][CH3:18])=[CH:6][C:7]3[C:8]([CH3:16])([CH3:15])[CH2:9][CH2:10][C:11]([CH3:13])([CH3:14])[C:12]=3[C:3]=2[O:2][CH3:1])=[CH:28][CH:27]=1

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 68116919HCID 68116919, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70389259HCID 70389259, compoundYield 53.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

3.8 g (10 millimoles) of the benzyl alcohol derivative from Example 27, dissolved in 10 ml of dry dimethylformamide, were added dropwise to a suspension of 0.3 g (11 millimoles) of sodium hydride in 15 ml of dry dimethylformamide. The mixture was stirred until evolution of hydrogen had ended (after about 1 hour), and 1.56 g (11 millimoles) of iodomethane were then added dropwise while cooling with ice. The mixture was then heated at 60° C. for 5 hours. On the next day, water was added dropwise, and the precipitated solid was filtered off under suction, and dissolved in methanol at elevated temperature. When the solution was cooled to room temperature, 2 phases formed. The upper (methanol) phase was heated once again and then placed in a refrigerator. The precipitated crystals were filtered off under suction and dried. 2.1 g of the title compound of melting point 66°-68° C. were obtained in this manner.

Workup

  1. additionwere then added dropwise
  2. temperaturewhile cooling with ice
  3. filtrationthe precipitated solid was filtered off under suction
  4. dissolutiondissolved in methanol at elevated temperature
  5. temperatureWhen the solution was cooled to room temperature
  6. custom2 phases formed
  7. filtrationThe precipitated crystals were filtered off under suction
  8. customdried

Sources & evidence

ORD record
ord-44d7ad29f6e243fcac15d7e3c9e1a22e
Source dataset
uspto-grants-1989_01
Patent number
US04801733

Reaction notes

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