Methyl iodide → HCID 67099866, compound

HRID 2078135Notes

Reaction equation

HRID 2078135 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([CH2:11][CH3:12])[C:9]#[N:10])[CH:5]=[CH:6][CH:7]=1.[CH3:13]I.[H-].[Na+]>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([CH3:13])([CH2:11][CH3:12])[C:9]#[N:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58951694HCID 58951694, compound

Product 1

HCID 67099866HCID 67099866, compoundYield 110%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 2-(3-chlorophenyl)butanenitrile (4.69 g, 26 mmol) and MeI (2.0 mL, 31 mmol) in DMSO (15 mL) was added dropwise to a stirred solution of NaH (60% dispersion in mineral oil (1.3 g, 31 mmol)) in DMSO (35 mL) at 0° C. under a nitrogen atmosphere. The reaction mixture was stirred for 30 minutes at 0° C. and then brought to room temperature and stirred for 15 hours. The reaction mixture was quenched with water carefully and then diluted with EtOAc. The organic layer was separated, washed with water (2×) and brine, dried (MgSO4), and concentrated in vacuo to give the desired compound as a light yellow oil (5.54 g).

Workup

  1. custombrought to room temperature
  2. stirringstirred for 15 hours
  3. customThe reaction mixture was quenched with water carefully
  4. additiondiluted with EtOAc
  5. customThe organic layer was separated
  6. washwashed with water (2×) and brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9740901d3c1e423f925d6e05cff673ea
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

Loading…