Water → 25310-30-9

HRID 1710886Notes

Reaction equation

HRID 1710886 reaction equation
CO[CH:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:4]#[N:5].[H-].[Na+].[CH3:14]I.O.C1C[O:20][CH2:19]C1>>[CH3:19][O:20][C:10]1[CH:11]=[C:6]([CH:3]([CH3:14])[C:4]#[N:5])[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 3200562-Methoxy-2-phenylacetonitrile

Product 1

HCID 1361587025310-30-9Yield 44%

Procedure

To a solution of methoxyphenyl acetonitrile (4.0 g, 27 mmol) in THF at room temperature was added NaH (1.19 g, 30 mmol). After 20 min, MeI (1.68 mL, 27 mmol) was added. The reaction was stirred at room temperature overnight. H2O was added to quench the reaction. It was concentrated and diluted with Ether. The ether was washed with 1N HCl, saturated NaCl, dried and concentrated to give a crude mixture which was purified by column chromatography on ISCO (120 g) with 0-30% hexanes in ethyl acetate over 28 min to yield 2-(3-methoxyphenyl)-propanenitrile (1.9 g, 44% yield) as a light brownish oil. HPLC retention time (Method C)=2.47 min. LC/MS (ESI) (M+H)+=162.16. 1H NMR (CDCl3, 400 MHz) δ ppm 1.64 (d, J=7.34 Hz, 3H), 3.82 (s, 3H), 3.85-3.92 (m, 1H), 6.83-6.96 (m, 2H), 7.24-7.34 (m, 2H).

Workup

  1. customto quench
  2. customthe reaction
  3. concentrationIt was concentrated
  4. additiondiluted with Ether
  5. washThe ether was washed with 1N HCl, saturated NaCl
  6. customdried
  7. concentrationconcentrated
  8. customto give a crude mixture which
  9. customwas purified by column chromatography on ISCO (120 g) with 0-30% hexanes in ethyl acetate over 28 min

Sources & evidence

ORD record
ord-3668d9dafe774d39967e88c51cbb07a8
Source dataset
uspto-grants-2010_09
Patent number
US07790745B2

Reaction notes

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