Water → 4-[(2-Oxocyclohexyl)methyl]benzonitrile

HRID 488730Notes

Reaction equation

HRID 488730 reaction equation
[Na+].[I-].Br[CH2:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1.N1([C:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]=2)CCCC1.[OH2:24]>CCO>[O:24]=[C:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]1[CH2:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 707681-Pyrrolidino-1-cyclohexeneHCID 869964-(Bromomethyl)benzonitrile

Product 1

HCID 221478034-[(2-Oxocyclohexyl)methyl]benzonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

NaI (1 g) was added to a solution of 4-Bromomethyl benzonitrile (12.9 g, 0.066 mol) and 1-(pyrrolidino-1-cyclohexene (10 g, 0.066 mol) in EtOH (150 ml). After 1 night at RT, the reaction mixture was poured into water (500 ml) and extracted twice with EtOAc. The organic phase was washed twice with water, dried over magnesium sulfate and concentrated to yield 4-[(2-oxocyclohexyl)methyl]-benzonitrile (7.06 g) as a yellow oil. 1H NMR (CDCl3): 7.60 (2H, d), 7.30 (2H, d), 3.25 (1H, dd), 2.7-2.2 (4H, m), 2.2-1.2 (6H, m).

Workup

  1. waitAfter 1 night at RT
  2. extractionextracted twice with EtOAc
  3. washThe organic phase was washed twice with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d7811661b48f489f8a8fea3b58843a90
Source dataset
uspto-grants-2005_12
Patent number
US06974815B2

Reaction notes

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