Iodoethane → 2-(Thiophen-3-yl)butanenitrile

HRID 44682Notes

Reaction equation

HRID 44682 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH2:6][C:7]#[N:8])=[CH:2]1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.I[CH2:20][CH3:21]>C1COCC1>[S:1]1[CH:5]=[CH:4][C:3]([CH:6]([CH2:20][CH3:21])[C:7]#[N:8])=[CH:2]1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 837303-ThienylacetonitrileHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 666434802-(Thiophen-3-yl)butanenitrileYield 18.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A cooled solution of 2-(3-thienyl)acetonitrile (3.144 g, 25.52 mmol) in THF (30 mL) under nitrogen was treated with LHMDS in THF (22.70 g, 25.51 mL of 1 M, 25.50 mmol) dropwise over a period of 20 minutes. The mixture was allowed to stir for 30 minutes and then treated with iodoethane (4.180 g, 2.144 mL, 26.80 mmol) dropwise. The reaction was stirred at RT for a further hour and then quenched by the addition of MeOH and concentrated in vacuo. The residue was diluted with water and extracted with EtOAc (2×). The combined organics were dried (MgSO4), filtered, concentrated and purified by column chromatography (6:1 Petroleum ether/EtOAc) to give the product as an oil (708 mg, 18% Yield). 1H NMR (CDCl3, 400 MHz) δ 1.08 (3H, t), 1.93-2.00 (2H, q), 3.86 (1H, m), 7.03 (1H, m), 7.25 (1H, m), 7.37 (1H, m)

Workup

  1. stirringThe reaction was stirred at RT for a further hour
  2. customquenched by the addition of MeOH
  3. concentrationconcentrated in vacuo
  4. additionThe residue was diluted with water
  5. extractionextracted with EtOAc (2×)
  6. dry with materialThe combined organics were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by column chromatography (6:1 Petroleum ether/EtOAc)

Sources & evidence

ORD record
ord-a6e45d6af19041c9a05530cc0cd526d4
Source dataset
uspto-grants-2013_09
Patent number
US08541445B2

Reaction notes

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