Diisopropylamine → HCID 68997609, compound

HRID 230791Notes

Reaction equation

HRID 230791 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19].[CH:20]([C:22]1[CH:27]=[CH:26][C:25]([C:28]([O:30][CH3:31])=[O:29])=[CH:24][CH:23]=1)=[O:21].[Cl-].[NH4+]>C1COCC1.CCCCCC>[OH:21][CH:20]([C:22]1[CH:23]=[CH:24][C:25]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][CH:27]=1)[CH2:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][N:13]=1

Participants

8

Reactant 5

HCID 7912DiisopropylamineHCID 79752-MethylpyridineHCID 15294Methyl 4-FormylbenzoateHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

Product 1

HCID 68997609HCID 68997609, compoundYield 5.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

With cooling with ice, a hexane solution (48 mL) of 2.6 N n-butyllithium was added to a THF solution (300 mL) of diisopropylamine (18 mL), stirred at 0° C. for 5 minutes, and then cooled to −78° C. Next, 2-picoline (10 g) was dropwise added thereto, and stirred at that temperature for 30 minutes. THF solution (100 mL) of methyl 4-formylbenzenecarboxylate (17.6 g) was added thereto, and stirred at −78° C. for 30 minutes and then at room temperature for 4 hours. Aqueous saturated ammonium chloride solution was added to the reaction liquid, and extracted with ethyl acetate. The organic layer was washed with aqueous saturated ammonium chloride solution and saturated saline water, and dried with anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate=2/1) to obtain the entitled compound (1.5 g) as a colorless solid.

Workup

  1. temperatureWith cooling with ice
  2. temperaturecooled to −78° C
  3. stirringstirred at that temperature for 30 minutes
  4. stirringstirred at −78° C. for 30 minutes
  5. waitat room temperature for 4 hours
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with aqueous saturated ammonium chloride solution and saturated saline water
  8. dry with materialdried with anhydrous sodium sulfate
  9. customThe solvent was evaporated off under reduced pressure
  10. customthe resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-ea5f7147e070484e8a53793c790683cc
Source dataset
uspto-grants-2009_07
Patent number
US07566781B2

Reaction notes

Loading…