Acetonitrile → 3-Cyclopentyl-3-oxopropanenitrile

HRID 871480Notes

Reaction equation

HRID 871480 reaction equation
[CH:1]1([C:6]([O:8]C)=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:10](#[N:12])[CH3:11].[H-].[Na+]>O1CCCC1>[CH:1]1([C:6](=[O:8])[CH2:11][C:10]#[N:12])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 78365Methyl cyclopentanecarboxylate

Product 1

HCID 135921183-Cyclopentyl-3-oxopropanenitrileYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

According to the procedure described in Example 133A Step 1 methyl cyclopentanecarboxylate (4 g, 31.25 mmol), anhydrous acetonitrile (2.55 mL, 48.75 mmol) and sodium hydride, 60% in mineral oil, (1.95 g, 48.75 mmol) in anhydrous tetrahydrofuran (25 mL) were reacted to afford 3-cyclopentyl-3-oxopropanenitrile (3.97 g, 93%) as yellow oil, which was used directly in the next step without further purification. 1H NMR (300 MHz, CDCl3) δ 3.5 (s, 2H), 3.13-3.02 (m, 1H), 1.95-1.62 (m, 8H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-69b3cf78dc634cbf871a6a4e6e133d06
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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