4-Methylpyridine → HCID 65582892, compound

HRID 2278409Notes

Reaction equation

HRID 2278409 reaction equation
C([N-]C(C)C)(C)C.[Li+].[N:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1.CN(OC)[C:18]([C:20]1[CH:24]=[CH:23][O:22][C:21]=1[CH3:25])=[O:19]>O1CCCC1.[Cl-].[Na+].O>[CH3:25][C:21]1[O:22][CH:23]=[CH:24][C:20]=1[C:18](=[O:19])[CH2:15][C:12]1[CH:13]=[CH:14][N:9]=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 79634-MethylpyridineHCID 2724682Lithium diisopropylamideHCID 21082665HCID 21082665, compound

Product 1

HCID 65582892HCID 65582892, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of lithium diisopropylamide (2M solution in THF/heptane/ethylbenzene) (12.00 ml, 24.00 mmol) in tetrahydrofuran (20 ml) at −78° C. under argon was added 4-picoline (1.946 ml, 20 mmol). The reaction mixture was stirred at −78° C. for 15 minutes and a solution of N,2-dimethyl-N-(methyloxy)-3-furancarboxamide (3.38 g, 20.00 mmol) in tetrahydrofuran (5 ml) was added dropwise. The solution was allowed to warm to room temperature over 2 hours. Brine was added and the mixture was extracted with dichloromethane. The organic layer was separated and washed with saturated sodium hydrogen carbonate solution, water and brine, dried and evaporated to give the title compound as a solid (3.72 g, 92%). LC/MS [M+H]+=202.

Workup

  1. temperatureto warm to room temperature over 2 hours
  2. extractionthe mixture was extracted with dichloromethane
  3. customThe organic layer was separated
  4. washwashed with saturated sodium hydrogen carbonate solution, water and brine
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-1254b63ec52146e29083db2a260f5530
Source dataset
uspto-grants-2015_09
Patent number
US09133178B2

Reaction notes

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