Ammonium Chloride → HCID 68507978, compound

HRID 1877283Notes

Reaction equation

HRID 1877283 reaction equation
[CH3:1][C:2]1[C:3]([CH:17]=[O:18])=[CH:4][N:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=2)[CH:6]=1.[CH:19]1([Mg]Br)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.O1CCCC1.[Cl-].[NH4+]>O1CCCC1>[CH:19]1([CH:17]([C:3]2[C:2]([CH3:1])=[CH:6][N:5]([C:7]3[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:14])[F:15])[CH:8]=3)[CH:4]=2)[OH:18])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 86646399HCID 86646399, compoundHCID 178420632HCID 178420632, compound

Product 1

HCID 68507978HCID 68507978, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-methyl-1-[3-(trifluoromethyl)phenyl]-1H-pyrrole-3-carbaldehyde (2.3 g) synthesized above in tetrahydrofuran (20 mL) was added dropwise 1M cyclohexylmagnesium bromide-tetrahydrofuran solution (12 mL) at 0° C. After stirring at 0° C. for 1 hr, an aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate. The extract was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4, volume ratio) to give the title compound (1.8 g, 52%) as a colorless solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. concentrationThe extract was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4, volume ratio)

Sources & evidence

ORD record
ord-a7c7ec7564114114a0bae6d01bce5598
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

Loading…