Acetonitrile → HCID 69095655, compound

HRID 2177659Notes

Reaction equation

HRID 2177659 reaction equation
[Li]CCCC.[C:6](#[N:8])[CH3:7].CO[C:11](=[O:21])[C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[N:14][C:13]=1[O:19][CH3:20]>C1COCC1>[CH3:20][O:19][C:13]1[C:12]([C:11](=[O:21])[CH2:7][C:6]#[N:8])=[CH:17][CH:16]=[C:15]([CH3:18])[N:14]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 10910170METHYL 2-METHOXY-6-METHYLPYRIDINE-3-CARBOXYLATEHCID 178418339Butyllithium

Product 1

HCID 69095655HCID 69095655, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

n-BuLi (1.2 M, 96.0 mL, 115.6 mmol) is added to a solution of acetonitrile (6.08 mL, 115.4 mmol) in THF (300 mL) at −78° C. and allowed to stir for 30 min at −78° C. 2-Methoxy-6-methyl-nicotinic acid methyl ester (20 g, 105.1 mmol) THE (200 mL) is added and stirred at −78° C. for another 30 min. The reaction mixture is quenched at −78° C. with water (500 mL) and washed with EtOAc (2×250 mL). The aqueous layer is separated and evaporated. This is co-distilled twice with toluene to obtain 3-(2-methoxy-6-methyl-pyridin-3-yl)-3-oxo-propionitrile. Yield=21.4 g (crude). ES/MS m/z 191.1 [M+H]+.

Workup

  1. stirringstirred at −78° C. for another 30 min
  2. customThe reaction mixture is quenched at −78° C. with water (500 mL)
  3. washwashed with EtOAc (2×250 mL)
  4. customThe aqueous layer is separated
  5. customevaporated

Sources & evidence

ORD record
ord-54badb3729b34ef4b23720fb8ccfeb60
Source dataset
uspto-grants-2015_06
Patent number
US09067920B2

Reaction notes

Loading…