Water → 5-Chloro-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile

HRID 1415981Notes

Reaction equation

HRID 1415981 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([CH:14]([CH3:16])[CH3:15])[C:12]#[N:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[NH2-].[Na+].[Cl:19][CH2:20][CH2:21][CH2:22]I.O>C1(C)C=CC=CC=1>[Cl:19][CH2:20][CH2:21][CH2:22][C:11]([C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)([CH:14]([CH3:16])[CH3:15])[C:12]#[N:13]

Participants

6

Reactant 4

HCID 962WaterHCID 24533Sodium amideHCID 813631-Chloro-3-iodopropaneHCID 893962-(3,4-Dimethoxyphenyl)-3-methylbutanenitrile

Product 1

HCID 6199535-Chloro-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrileYield 85.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-(3,4-dimethoxyphenyl)-3-methylbutanenitrile (1.21 g, 5.52 mmol) was added to a suspension of sodium amide (0.59 g, 14.4 mmol) in toluene (12 ml). The mixture was then heated to reflux for 2 hours before the addition of 1-chloro-3-iodopropane (0.9 ml, 8.3 mmol). The mixture was cooled to room temperature over 80 minutes, and worked up by addition of water. The product was extracted with methyl-t-butyl ether (MTBE). After usual work-up, including drying the organic extract using MgSO4 and concentrating under reduced pressure the product was purified on column chromatography eluting with (ethyl acetate: light petroleum (b.p. 40 -60° C.) =1:2), to give 1.4g (82% yield) of the required product.

Workup

  1. temperatureThe mixture was then heated
  2. extractionThe product was extracted with methyl-t-butyl ether (MTBE)
  3. customAfter usual work-up, including drying the
  4. extractionorganic extract
  5. concentrationconcentrating under reduced pressure the product
  6. customwas purified on column chromatography
  7. washeluting with (ethyl acetate: light petroleum (b.p. 40 -60° C.) =1:2)

Sources & evidence

ORD record
ord-ba42bd1cc01544fb97c95a7ea0f75a96
Source dataset
uspto-grants-1999_06
Patent number
US05910601

Reaction notes

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