Water → 2-[5-Methoxy-2-(4-methoxy-phenyl)-benzofuran-7-yl]-2-methyl-propionitrile

HRID 1835983Notes

Reaction equation

HRID 1835983 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][C:21]#N)[C:6]2[O:10][C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=[CH:8][C:7]=2[CH:19]=1.[OH-].[K+].[CH3:25]I.O.C[N:29]([CH3:32])C=O>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:20]([CH3:21])([CH3:25])[C:32]#[N:29])[C:6]2[O:10][C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=[CH:8][C:7]=2[CH:19]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 10308348HCID 10308348, compound

Product 1

HCID 102151342-[5-Methoxy-2-(4-methoxy-phenyl)-benzofuran-7-yl]-2-methyl-propionitrileYield 78%

Procedure

To a solution of acetonitrile 18 (0.054 g, 0.184 mmole) in 5 mL dimethylformamide was added pulverized potassium hydroxide (0.024 g, 0.390 mmole) and methyl iodide (0.0552 g, 0.0391 mmole). After stirring at rt for 2 hours, the reaction mixture was poured into water and extracted with ethyl acetate. The combined organic phases were washed with saturated sodium bicarbonate, water, brine, and dried with magnesium sulfate. The organic phases were concentrated and the residue was loaded on to silica gel and chromatographed with silica gel (hexanes:ethyl acetate, 95:5) to afford 0.046 g (78%) of methyl-propionitrile 20 as a yellow solid: Mp=146-148° C.; 1H NMR (DMSO-d6) δ 7.87 (d, 2 H, J=8.8 Hz), 7.26 (s, 1 H),), 7.15 (d, 1 H, J=2.4 Hz), 7.10 (d, 2 H, J=8.9 Hz), 6.86 (d, 1 H, J=2.4 Hz), 3.82 (s, 3 H), 3.81 (s, 3 H), 1.89 (s, 6 H); MS 322 (M+H)+

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic phases were washed with saturated sodium bicarbonate, water, brine
  3. dry with materialdried with magnesium sulfate
  4. concentrationThe organic phases were concentrated
  5. customchromatographed with silica gel (hexanes:ethyl acetate, 95:5)

Sources & evidence

ORD record
ord-562db3a3bc214b84b6ca46090c10c363
Source dataset
uspto-grants-2004_08
Patent number
US06774248B2

Reaction notes

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