Water → 4-(5-Chloropentanoyl)benzonitrile

HRID 747708Notes

Reaction equation

HRID 747708 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[Cl:22][CH2:23][CH2:24][CH2:25]I.O>O1CCCC1>[Cl:22][CH2:23][CH2:24][CH2:25][CH2:2][C:1]([C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1)=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 740444'-CyanoacetophenoneHCID 813631-Chloro-3-iodopropaneHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 177891304-(5-Chloropentanoyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1 g (6.9 mmol) of 4-acetylbenzonitrile was dissolved in 8 ml of tetrahydrofuran. 9 ml of lithium bis(trimethylsilyl)amide (1 M solution in hexane) was gradually added to the solution at −70° C. and they were stirred for 30 minutes. 1.43 g (7 mmol) of 1-chloro-3-iodopropane dissolved in 6 ml of tetrahydrofuran was added thereto, and the resultant mixture was stirred at room temperature overnight. The reaction liquid was poured into water. After the extraction with ethyl acetate, the extract was washed with 1 N hydrochloric acid and saturated aqueous common salt solution, and then dried over powdery magnesium sulfate. The solvent was evaporated, and the residue was purified by the silica gel chromatography to obtain the title compound.

Workup

  1. additionwas added
  2. customThe reaction liquid
  3. extractionAfter the extraction with ethyl acetate
  4. washthe extract was washed with 1 N hydrochloric acid and saturated aqueous common salt solution
  5. dry with materialdried over powdery magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was purified by the silica gel chromatography

Sources & evidence

ORD record
ord-32d3485eccad435781cb0e527ae4d2a9
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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