Diethyl Ether → HCID 23154981, compound

HRID 1912885Notes

Reaction equation

HRID 1912885 reaction equation
CCOCC.Br[C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:17]([CH3:18])=[CH:16][CH:15]=[C:14]2[CH3:19])=[CH:9][C:8]=1[C:20]([F:23])([F:22])[F:21].C([Li])CCC.[CH:29]([C:31]1[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=1)=[O:30]>O1CCCC1>[CH3:19][C:14]1[N:13]([C:10]2[CH:11]=[CH:12][C:7]([CH:29]([C:31]3[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=3)[OH:30])=[C:8]([C:20]([F:23])([F:22])[F:21])[CH:9]=2)[C:17]([CH3:18])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 133894-PyridinecarboxaldehydeHCID 23154931HCID 23154931, compoundHCID 178418339Butyllithium

Product 1

HCID 23154981HCID 23154981, compoundYield 66.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 12 mL of an anhydrous ether solution of 1.08 g (3.4 mmol) of 1-(4-bromo-3-trifluoromethyl-phenyl)-2,5-dimethyl-1H-pyrrole, 1.4 mL of n-butyllithium (a tetrahydrofuran solution, 2.44 M) was added at one time at −60° C. and the mixture solution was stirred for one hour. Then, 5 mL of a tetrahydrofuran solution of 350 mg (3.27 mmol) of 4-formylpyridine was added thereto at −60° C. and the mixture solution was stirred while raising the temperature to room temperature over one hour. The reaction solution was partitioned between a saturated ammonium chloride aqueous solution and ethyl acetate and the organic layer was washed with a saturated sodium chloride solution and concentrated under reduced pressure. The obtained residue was purified by a silica gel column (n-hexane:ethyl acetate=1:1) to obtain 754 mg (66%) of a target product as a pale yellow oil.

Workup

  1. stirringat −60° C. and the mixture solution was stirred
  2. customThe reaction solution was partitioned between a saturated ammonium chloride aqueous solution and ethyl acetate
  3. washthe organic layer was washed with a saturated sodium chloride solution
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by a silica gel column (n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-c35e5513e58b4209bec7831539cff1bc
Source dataset
uspto-grants-2013_12
Patent number
US08609656B2

Reaction notes

Loading…