Water → HCID 59511929, compound

HRID 1157677Notes

Reaction equation

HRID 1157677 reaction equation
CON(C)[C:4](=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[N:7][CH:6]=1.[CH3:13][C:14]([CH3:18])=[CH:15][Mg]Br.[Cl-].[NH4+].O>C1COCC1>[CH3:15][C:14]([CH3:18])=[CH:13][C:4]([C:5]1[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=1)=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 10558996N-Methoxy-N-methylnicotinamideHCID 178448304HCID 178448304, compound

Product 1

HCID 59511929HCID 59511929, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-methoxy-N-methylnicotinamide (500 mg, 3.0 mmol) in anhydrous THF (3.5 mL) under nitrogen at −78° C. add 2-methyl propenyl magnesium bromide (12 mL, 6.0 mmol, 0.5 M in THF) dropwise. After one hour at −78° C., allow to reach room temperature. After 2 h, add saturated aqueous ammonium chloride. (10 mL) and water (2 mL). Extract with ethyl acetate three times, dry the combined organic phases with anhydrous sodium sulfate and concentrate to obtain 442 mg (91%) of the title compound as a yellow oil.

Workup

  1. customto reach room temperature
  2. waitAfter 2 h
  3. extractionExtract with ethyl acetate three times
  4. dry with materialdry the combined organic phases with anhydrous sodium sulfate
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-b7e210ba430448a5beabbd23fe949a1c
Source dataset
uspto-grants-2010_10
Patent number
US07807691B2

Reaction notes

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