Diisopropylamine → HCID 23103606, compound

HRID 2116500Notes

Reaction equation

HRID 2116500 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[Cl:13][C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1.[CH2:20]([C:22]1[CH:29]=[CH:28][C:25]([CH:26]=[O:27])=[CH:24][CH:23]=1)[CH3:21].[Cl-].[NH4+]>C1COCC1.CCCCCC>[Cl:13][C:14]1[CH:19]=[CH:18][N:17]=[CH:16][C:15]=1[CH:26]([C:25]1[CH:28]=[CH:29][C:22]([CH2:20][CH3:21])=[CH:23][CH:24]=1)[OH:27]

Participants

8

Reactant 5

HCID 7912DiisopropylamineHCID 122884-ChloropyridineHCID 208614-EthylbenzaldehydeHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

Product 1

HCID 23103606HCID 23103606, compoundYield 71.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent4×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

A 1.58 M n-hexane solution of n-butyllithium (30.1 mL, 0.0476 mol) and THF (125 mL) were mixed and a solution of diisopropylamine (6.67 mL, 0.0476 mol) in THF (25 mL) was added dropwise thereto at −20° C., followed by stirring for 25 minutes. After cooling the reaction mixture to −78° C., a solution of 4-chloropyridine (5.4 g, 0.0476 mol) in THF (25 mL) was added dropwise. After 15 minutes, a solution of 4-ethylbenzaldehyde (6.4 g, 0.0477 mol) in THF (25 mL) was added dropwise and stirred for 30 minutes. After warming the reaction mixture to room temperature, saturated aqueous ammonium chloride was added and the resulting mixture was then extracted twice with ethyl acetate. The combined organic layers were washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to give (4-chloropyridin-3-yl)-(4-ethylphenyl)methanol (8.4 g, 71%) as a light-yellow crystal.

Workup

  1. customat −20° C.
  2. waitAfter 15 minutes
  3. stirringstirred for 30 minutes
  4. temperatureAfter warming the reaction mixture to room temperature
  5. extractionthe resulting mixture was then extracted twice with ethyl acetate
  6. washThe combined organic layers were washed with saturated aqueous sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationAfter the solvent was distilled off under reduced pressure
  9. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-32064650d6b5413c8ffd3d5233e31b55
Source dataset
uspto-grants-2008_10
Patent number
US07439232B2

Reaction notes

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