Dimethylformamide → 157763-70-7

HRID 1258054Notes

Reaction equation

HRID 1258054 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH2:6][C:7]#N)=[CH:2]1.[CH3:9]I.[H-].[Na+].C[N:14]([CH:16]=O)C>>[CH3:9][C:6]([C:3]1[CH:4]=[CH:5][S:1][CH:2]=1)([CH3:7])[C:16]#[N:14]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 837303-Thienylacetonitrile

Product 1

HCID 68959143157763-70-7

Conditions

Temperature
0 °C

Procedure

To a solution of thiophene-3-acetonitrile (6.15 g, 50 mmol) and MeI (12.5 mL, 4 equiv) in DMF (200 mL) was added sodium hydride (6 g, 60%, 3 equiv) at 0° C. under nitrogen and the reaction mixture was stirred for 3 h at 0° C. It was then quenched with water and extracted with hexane (3×100 mL). The combined organic layer was washed with water and dried over MgSO4. Evaporation of solvent afforded 2-methyl-2-thiophen-3-yl-propionitrile as an oil, which was used in next step without further purification. 1H-NMR(CDCl3): δ 8.02 (1H, m), 7.35 (1H, dd), 7.12 (1H, dd), 2.96 (3H, s), 2.89 (3H, s).

Workup

  1. customIt was then quenched with water
  2. extractionextracted with hexane (3×100 mL)
  3. washThe combined organic layer was washed with water
  4. dry with materialdried over MgSO4
  5. customEvaporation of solvent

Sources & evidence

ORD record
ord-33bfaf82917f4f169eeabd03e50a086e
Source dataset
uspto-grants-2013_06
Patent number
US08466143B2

Reaction notes

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