Diisopropylamine → HCID 10368088, compound

HRID 1033896Notes

Reaction equation

HRID 1033896 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[CH2:13]1[O:21][C:20]2[CH:19]=[CH:18][C:17]([CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:16][C:15]=2[O:14]1.C1OC2C=CC(C=O)=CC=2O1.COC(CP(OC)(OC)=O)=O.[H-].[Na+].[H][H].[CH2:54]([C:58]1[N:59]([CH2:65][C:66]2[CH:71]=[CH:70][CH:69]=[CH:68][C:67]=2[Cl:72])[C:60]([CH:63]=[O:64])=[CH:61][N:62]=1)[CH2:55][CH2:56][CH3:57]>O1CCCC1.COCCOC.[Pd].C(OCC)(=O)C>[CH3:27][O:26][C:24](=[O:25])[CH:23]([CH2:22][C:17]1[CH:18]=[CH:19][C:20]2[O:21][CH2:13][O:14][C:15]=2[CH:16]=1)[CH:63]([C:60]1[N:59]([CH2:65][C:66]2[CH:71]=[CH:70][CH:69]=[CH:68][C:67]=2[Cl:72])[C:58]([CH2:54][CH2:55][CH2:56][CH3:57])=[N:62][CH:61]=1)[OH:64]

Participants

13

Reactant 8

HCID 7912DiisopropylamineHCID 8438PiperonalHCID 24758Sodium hydrideHCID 80029Trimethyl phosphonoacetateHCID 10081775methyl 3-(3,4-methylenedioxyphenyl)-propionateHCID 101075301H-Imidazole-5-carboxaldehyde, 2-butyl-1-[(2-chlorophenyl)methyl]-HCID 178418339ButyllithiumHCID 178418361HCID 178418361, compound

Product 1

HCID 10368088HCID 10368088, compoundYield 31%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent3×HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

In tetrahydrofuran (20 mL) was placed diisopropylamine (1.41 mL, 10.0 mmol). The mixture was cooled to 0° C. under argon and in n-butyl lithium (4 mL of 2.5 M in toluene, 10.08 mmol) was added. The reaction was stirred at 0° C. for 0.5 hour, then cooled to -78° C. A solution of methyl 3-(3,4-methylenedioxyphenyl)propanoate (2 g, 9.6 mmol) (prepared by reaction of 3,4-methylenedioxybenzaldehyde with trimethyl phosphonoacetate in the presence of sodium hydride in ethylene glycol dimethyl ether, followed by catalytic hydrogenation with 10% palladium on carbon at 3 atmospheres of hydrogen in an ethyl acetate solution) in tetrahydrofuran (15 mL) was added, and the mixture was stirred at -78° C. for 1 hour. A solution of 2-n-butyl-1-(2-chlorophenyl)methyl-1H-imidazol-5-carboxaldehyde (2.49 g, 9 mmol) in tetrahydrofuran was added, and the mixture was stirred for 30 minutes at -78° C. The reaction was quenched with ammonium chloride solution, and the product was extracted into ethyl acetate. The concentrated product was flash chromatographed with 6:4 ethyl acetate/hexane to yield 1.33 g (31%) of the title compound as an oil.

Workup

  1. additionwas added
  2. temperaturecooled to -78° C
  3. additionwas added
  4. stirringthe mixture was stirred at -78° C. for 1 hour
  5. stirringthe mixture was stirred for 30 minutes at -78° C
  6. customThe reaction was quenched with ammonium chloride solution
  7. extractionthe product was extracted into ethyl acetate
  8. customchromatographed with 6:4 ethyl acetate/hexane

Sources & evidence

ORD record
ord-fe6920c066e3421e92c6f9f36e37fc58
Source dataset
uspto-grants-1994_05
Patent number
US05312828

Reaction notes

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