Methyl Benzoate → HCID 19969618, compound

HRID 974826Notes

Reaction equation

HRID 974826 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[N:4]=1)#[N:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[C:20](OC)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1COCC1>[C:1]([C:3]1[N:4]=[C:5]([CH2:9][C:20](=[O:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 7150Methyl BenzoateHCID 741826-Methylpyridine-2-carbonitrileHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 19969618HCID 19969618, compoundYield 13.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of 2-cyano-6-methylpyridine (9.7 g, 0.082 mol) in 400 ml of dry THF at -78° C. was added dropwise 90 ml of a 1M solution of lithium bis(trimethylsilyl)amide in THF. After stirring for 30 minutes a solution of methyl benzoate (30 ml, 0.245 mol) in 50 ml of THF was added dropwise. The resulting mixture was allowed to warm to room temperature and stirred overnight. The mixture was cooled to 0° C., quenched with 1N HCl, made basic with 15% NaOH solution, and extracted with ethyl acetate (3×). The organic layer was separated, dried, and concentrated to give crude material which was purified by chromatography on silica gel to give 2.5 g of the subtitle compound.

Workup

  1. additionwas added dropwise
  2. temperatureThe mixture was cooled to 0° C.
  3. customquenched with 1N HCl
  4. extractionextracted with ethyl acetate (3×)
  5. customThe organic layer was separated
  6. customdried
  7. concentrationconcentrated
  8. customto give crude material which
  9. customwas purified by chromatography on silica gel

Sources & evidence

ORD record
ord-c870110cb064496881d9e677e36b9367
Source dataset
uspto-grants-1997_03
Patent number
US05607935

Reaction notes

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