Methyl iodide → HCID 13075147, compound

HRID 602760Notes

Reaction equation

HRID 602760 reaction equation
[C:1]1([S:7]([CH:10]([CH:13]2[CH2:18][CH2:17][CH2:16][C:15](=[O:19])[CH2:14]2)[C:11]#[N:12])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:22]I>CN(C=O)C>[C:1]1([S:7]([C:10]([CH:13]2[CH2:18][CH2:17][CH2:16][C:15](=[O:19])[CH2:14]2)([CH3:22])[C:11]#[N:12])(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 13075145HCID 13075145, compound

Product 1

HCID 13075147HCID 13075147, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.0 g (0.014 mol) of benzenesulfonyl-(3-oxo-cyclohexyl)-acetonitrile in 40 mL of DMF were treated with 0.69 g (0.016 mol, 1.1 eq) of NaH (55% in oil) portionwise within 30 min at 0° C. 3.07 g (0.022 mol, 1.5 eq) of methyliodide were added, and the ice bath was removed. After 2 hours, the reaction mixture was poured into water and extracted with EtOAc. The combined organic phases were dried over Na2SO4, filtered and evaporated. Column chromatography over silica gel with AcOEt/heptane 1:1 afforded 4 g (98%) of 2-benzenesulfonyl-2-(3-oxo-cyclohexyl)-propionitrile as a racemic mixture of diastereomers, white solid, MS: 292 (MH+).

Workup

  1. customthe ice bath was removed
  2. additionthe reaction mixture was poured into water
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-d0415af82b4d4addbe0d06a0df945dde
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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