Dimethylformamide → 5-(4-Chlorobenzyl)-5-cyano-2,2-dimethylcyclopentanone

HRID 1699124Notes

Reaction equation

HRID 1699124 reaction equation
[H-].[Na+].C([CH:5]1[CH2:9][CH2:8][C:7](=[O:10])[C:6]1([CH3:12])[CH3:11])#N.[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Cl)=[CH:16][CH:15]=1.CCCCCC.[CH3:28][N:29](C)C=O>>[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][C:8]2([C:28]#[N:29])[C:7](=[O:10])[C:6]([CH3:11])([CH3:12])[CH2:5][CH2:9]2)=[CH:16][CH:15]=1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 8058HexaneHCID 24758Sodium hydrideHCID 18323274HCID 18323274, compound

Product 1

HCID 112769975-(4-Chlorobenzyl)-5-cyano-2,2-dimethylcyclopentanoneYield 72.6%

Procedure

A 60% mineral oil suspension of sodium hydride (12.7 g, 0.31 mole) in dimethylformamide under nitrogen, is treated with cyano-2,2-dimethylcyclopentanone over a 50 minute period at ice-bath temperatures, then with a solution of 4-chloro-benzyl chloride (50.2 g, 0.31 mole) over a 30 minute period, stirred for 5 hours and quenched with water. The resultant mixture is extracted with ethyl acetate. The extracts are combined, washed with water and concentrated in vacuo to afford a solid residue. The residue is titurated with hexane to afford the title product as white crystals, 59.3 g (72.6% yield), mp 101°-103° C., identified by gas chromatography.

Workup

  1. customquenched with water
  2. extractionThe resultant mixture is extracted with ethyl acetate
  3. washwashed with water
  4. concentrationconcentrated in vacuo
  5. customto afford a solid residue

Sources & evidence

ORD record
ord-6e24075084b24ea6afab7a87b69d1caa
Source dataset
uspto-grants-2002_02
Patent number
US06344580B1

Reaction notes

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