Sodium hydride → 2-(5-Bromo-alpha-cyano-2-methoxymethoxybenzyl)-3-methoxymethoxypyridine

HRID 862059Notes

Reaction equation

HRID 862059 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH2:12][O:13][CH3:14])=[C:6]([CH:10]=1)[CH2:7][C:8]#[N:9].Br[C:16]1[C:21]([O:22][CH2:23][O:24][CH3:25])=[CH:20][CH:19]=[CH:18][N:17]=1.C1(C)C=CC(S([O-])=O)=CC=1.[Na+].[H-].[Na+]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH2:12][O:13][CH3:14])=[C:6]([CH:10]=1)[CH:7]([C:16]1[C:21]([O:22][CH2:23][O:24][CH3:25])=[CH:20][CH:19]=[CH:18][N:17]=1)[C:8]#[N:9]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 2723791Sodium p-toluenesulfinateHCID 115865732-Bromo-3-(methoxymethoxy)pyridineHCID 197016225-Bromo-2-methoxymethoxybenzyl cyanide

Product 1

HCID 197015562-(5-Bromo-alpha-cyano-2-methoxymethoxybenzyl)-3-methoxymethoxypyridineYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 5-bromo-2-methoxymethoxybenzyl cyanide (2.10 g), 2-bromo-3-methoxymethoxypyridine (1.79 g), sodium p-toluenesulfinate (0.44 g) and THF (30 ml) was added, at room temperature, 60% sodium hydride (0.69 g), followed by heating for 2 hours under reflux under argon atmosphere. The reaction mixture was poured into a saturated aqueous saline solution, which was subjected to extraction with ethyl acetate. The extract solution was washed with a saturated aqueous saline solution, dried (anhydrous sodium sulfate), and concentrated. The concentrate was purified by means of a silica gel column chromatography (eluted with ethyl acetate/hexane) to give 2-(5-bromo-α-cyano-2-methoxymethoxybenzyl)-3-methoxymethoxypyridine (2.58 g), whose physical properties and spectrum data are shown in Table 9 and Table 12.

Workup

  1. additionwas added, at room temperature
  2. temperatureby heating for 2 hours
  3. temperatureunder reflux under argon atmosphere
  4. additionThe reaction mixture was poured into a saturated aqueous saline solution, which
  5. extractionwas subjected to extraction with ethyl acetate
  6. washThe extract solution was washed with a saturated aqueous saline solution
  7. dry with materialdried (anhydrous sodium sulfate)
  8. concentrationconcentrated
  9. customThe concentrate was purified by means of a silica gel column chromatography (eluted with ethyl acetate/hexane)

Sources & evidence

ORD record
ord-fff40f42801b49158be897f1a385e4df
Source dataset
uspto-grants-1998_02
Patent number
US05716971

Reaction notes

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