Lithium Hydroxide → 1-Methyl-2-oxocyclopentane-1-carbonitrile

HRID 1408936Notes

Reaction equation

HRID 1408936 reaction equation
[OH-].[Li+].I[CH3:4].[O:5]=[C:6]1[CH2:10][CH2:9][CH2:8][CH:7]1[C:11]#[N:12]>O.CO>[CH3:4][C:7]1([C:11]#[N:12])[CH2:8][CH2:9][CH2:10][C:6]1=[O:5]

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 6328Methyl iodideHCID 98930Cyclopentanecarbonitrile, 2-oxo-

Product 1

HCID 132142491-Methyl-2-oxocyclopentane-1-carbonitrileYield 78.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A solution of lithium hydroxide (0.2226 g, 9.30 mmol) in water (5 mL) and iodomethane (0.591 mL, 9.46 mmol) were added to a stirred solution of 2-oxocyclopentanecarbonitrile (0.86 g, 7.88 mmol) in methanol (5 mL) at room temperature. The resulting mixture was heated to 50° C. for 1.5 h. The methanol solvent was removed in vacuo. The aqueous residue was extracted with ether (2×25 mL). The combined ether extracts were dried (Na2SO4), decanted and concentrated to give 1-methyl-2-oxocyclopentanecarbonitrile (0.76 g, 78% yield). 1H NMR (500 MHz, chloroform-d) δ ppm 2.63-2.74 (1 H, m), 2.43 (2 H, t, J=7.21 Hz), 1.59-1.93 (4 H, m), 1.34 (3 H, d, J=6.94 Hz).

Workup

  1. customThe methanol solvent was removed in vacuo
  2. extractionThe aqueous residue was extracted with ether (2×25 mL)
  3. dry with materialThe combined ether extracts were dried (Na2SO4)
  4. customdecanted
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9b5c2db5b88b4cbebd1f28d8243e934d
Source dataset
uspto-grants-2014_12
Patent number
US08921368B2

Reaction notes

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