Methyl iodide → HCID 18694287, compound

HRID 1870897Notes

Reaction equation

HRID 1870897 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([N:9]2[CH2:13][CH2:12][CH2:11][C:10]2=[O:14])[CH:6]=[CH:5][C:4]=1[C:15]1[CH:20]=[CH:19][C:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:17][CH:16]=1.[H-].[Na+].I[CH3:29]>CN(C=O)C.C(OCC)(=O)C>[CH3:29][O:1][CH2:2][C:3]1[CH:8]=[C:7]([N:9]2[CH2:13][CH2:12][CH2:11][C:10]2=[O:14])[CH:6]=[CH:5][C:4]=1[C:15]1[CH:16]=[CH:17][C:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 18694222HCID 18694222, compound

Product 1

HCID 18694287HCID 18694287, compoundYield 64.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 2'-hydroxymethyl-4'-(2-oxopyrrolidin-1-yl)biphenyl-4-carboxylate (D54) (0.51 g, 1.5 mmol) was stirred in dry DMF (8 ml) under argon. Sodium hydride (80% dispersion, 0.07 g, 2.3 mmol) was added, and the resulting suspension was stirred for 10 min. Iodomethane (0.19 ml, 3.0 mmol) was added; the mixture was stirred for 30 min, diluted with ethyl acetate, washed with water and brine, dried (Na2SO4) and evaporated to a yellow gum. Chromatography on silica gel, eluting with 0-50% ethyl acetate/dichloromethane, gave the title compound (0.34 g, 64%) as a colourless gum, solidifying on standing. A little methyl ester was also present.

Workup

  1. stirringthe mixture was stirred for 30 min
  2. washwashed with water and brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated to a yellow gum
  5. washChromatography on silica gel, eluting with 0-50% ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-9cc0795719af4c85b4323694dee40193
Source dataset
uspto-grants-2000_08
Patent number
US06100272

Reaction notes

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