Diisopropylamine → HCID 10926273, compound

HRID 1274063Notes

Reaction equation

HRID 1274063 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[Cl:13][C:14]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:15]=1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].[CH:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=1)=[O:29].[Cl-].[NH4+]>O1CCCC1.CCCCCC.O1CCCCC1>[Cl:13][C:14]1[C:26]([CH:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=2)[OH:29])=[C:25]([Cl:27])[CH:24]=[CH:23][C:15]=1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]

Participants

9

Reactant 5

HCID 7912DiisopropylamineHCID 142732-PyridinecarboxaldehydeHCID 25517Ammonium ChlorideHCID 4860726HCID 4860726, compoundHCID 178418339Butyllithium

Product 1

HCID 10926273HCID 10926273, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 8894TetrahydropyranSolvent

Procedure

At -20° C., 4.0 g (39.6 mmol) of diisopropylamine in 120 ml of tetrahydrofuran are stirred for 40 minutes with 25.0 ml (40.0 mmol) of a 1.6 M n-butyllithium solution in hexane. At -75° C., a solution of 10.0 g (40.5 mmol) of tert-butyl 2,4-dichlorobenzoate in 30 ml of tetrahydrofuran is added dropwise, and the mixture is stirred for 1.5 h. A solution of 4.3 g (40.5 mmol) of 2-formylpyridine in 20 ml of tetrahydropyran is added dropwise and the mixture is stirred at room temperature for 2.5 h. The mixture is poured into 500 ml of saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The combined extracts are washed with water, dried over sodium sulfate, filtered and freed from the solvent under reduced pressure. The crude product is purified by silica gel chromatography using cyclohexane/ethyl acetate. Yield: 7.5 g; 1H NMR, δ [ppm], (DMSO-d6): 1.5 (s), 6.5 (m), 7.2 (m); 7.5 (m), 7.9 (m), 8.4 (d)

Workup

  1. stirringthe mixture is stirred at room temperature for 2.5 h
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts are washed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customThe crude product is purified by silica gel chromatography

Sources & evidence

ORD record
ord-00a9e4aaee7c4bf8959cdbcf1c5e5a78
Source dataset
uspto-grants-2000_12
Patent number
US06156702

Reaction notes

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