Ammonium Chloride → HCID 59574603, compound

HRID 2092049Notes

Reaction equation

HRID 2092049 reaction equation
[Cl:1][C:2]1[C:3]([F:10])=[N:4][CH:5]=[CH:6][C:7]=1[CH:8]=[O:9].[CH3:11][Mg]Br.[Cl-].[NH4+]>O1CCCC1>[Cl:1][C:2]1[C:3]([F:10])=[N:4][CH:5]=[CH:6][C:7]=1[CH:8]([OH:9])[CH3:11]

Participants

5

Procedure

3-Chloro-2-fluoropyridine-4-carbaldehyde (56.1 mg, 0.35 mmol) in tetrahydrofuran (2 mL) was mixed with methylmagnesium bromide (0.98 M in tetrahydrofuran, 1.13 mL, 1.05 mmol) under −78° C., and the reaction mixture was warmed slowly to room temperature for 16 hours with stirring. After completion of the reaction, the reaction solution was mixed with saturated aqueous ammonium chloride and extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The resulting crude reaction product containing the desired product was used for the next step (64.7 mg).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe resulting crude reaction product

Sources & evidence

ORD record
ord-aa6c34562f314e3dafda66c497b752fa
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

Loading…