Sodium Cyanide → [2-(2,5-Dimethoxy-phenyl)-cyclopentyl]-acetonitrile

HRID 418924Notes

Reaction equation

HRID 418924 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[CH:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[CH2:16]OS(C)(=O)=O.[C-:22]#[N:23].[Na+]>CS(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[CH:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[CH2:16][C:22]#[N:23]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 72309417Methanesulfonic acid 2-(2,5-dimethoxy-phenyl)-cyclopentylmethyl ester

Product 1

HCID 66652057[2-(2,5-Dimethoxy-phenyl)-cyclopentyl]-acetonitrileYield 92.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

Dissolve methanesulfonic acid 2-(2,5-dimethoxy-phenyl)-cyclopentylmethyl ester (4.8 g, 15 mmol) in DMSO (25 ml), add sodium cyanide (12 g, 16 mmol), and heat at 100° C. over night. Cool to room temperature and quench with water and ethyl acetate. Separate layers, wash organic with water 3×, brine 2×, dry and concentrate to give the title compound (3.4 g 91%): 1H NMR (CDCl3) δ 6.79-6.72 (m,3H), 3.79 (s, 3H), 3.77 (s, 3H), 3.54-3.48 (m, 1H), 2.77-2.70 (m, 1H), 2.17-2.09 (m, 1H), 1.96-1.89 (m, 4H), 1.78-1.59 (m, 3H).

Workup

  1. temperatureCool to room temperature
  2. customquench with water and ethyl acetate
  3. washSeparate layers, wash organic with water 3×, brine 2×
  4. customdry
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-13215f3b08744f04a9917e521dc1f165
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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