Methyl iodide → 2-Methyl-2-(thiophen-3-yl)butanenitrile

HRID 44683Notes

Reaction equation

HRID 44683 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH:6]([CH2:9][CH3:10])[C:7]#[N:8])=[CH:2]1.[Li+].[CH3:12][Si]([N-][Si](C)(C)C)(C)C.IC>C1COCC1>[CH3:12][C:6]([C:3]1[CH:4]=[CH:5][S:1][CH:2]=1)([CH2:9][CH3:10])[C:7]#[N:8]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2733832Lithium HexamethyldisilazideHCID 666434802-(Thiophen-3-yl)butanenitrile

Product 1

HCID 666434282-Methyl-2-(thiophen-3-yl)butanenitrileYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A cooled solution of 2-(thiophen-3-yl)butanenitrile (708 mg, 4.682 mmol) in THF (15 mL) under nitrogen was treated with LHMDS in THF (4.375 g, 4.916 mL of 1 M, 4.916 mmol) dropwise. After 1 hour the reaction was treated with iodomethane (731.0 mg, 320.6 μL, 5.150 mmol) and then allowed to warm to RT. After 2.5 hours the reaction was quenched with MeOH and then concentrated in vacuo. The mixture was diluted with EtOAc/water and the two layers separated. The combined organics were dried (MgSO4), filtered, concentrated and purified by column chromatography (5:1 Petroleum ether/EtOAc) to give the product as a colourless oil (693 mg, 90% Yield).

Workup

  1. customAfter 2.5 hours the reaction was quenched with MeOH
  2. concentrationconcentrated in vacuo
  3. additionThe mixture was diluted with EtOAc/water
  4. customthe two layers separated
  5. dry with materialThe combined organics were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by column chromatography (5:1 Petroleum ether/EtOAc)

Sources & evidence

ORD record
ord-4ae311f02cb546589cf6a8883e715378
Source dataset
uspto-grants-2013_09
Patent number
US08541445B2

Reaction notes

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