Propanal → HCID 21252885, compound

HRID 850799Notes

Reaction equation

HRID 850799 reaction equation
[CH:1]1[CH:13]=[CH:12][C:11]2[C:14](=[O:17])[CH2:15][CH2:16][N:9]3[C:10]=2[C:2]=1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:8]=13.C([Li])CCC.[CH:23](=[O:26])[CH2:24][CH3:25].[Cl-].[NH4+]>O1CCCC1>[OH:26][CH:23]([C:15]1[C:14](=[O:17])[C:11]2[CH:12]=[CH:13][CH:1]=[C:2]3[C:10]=2[N:9]([CH:16]=1)[C:8]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]3=1)[CH2:24][CH3:25]

Participants

6

Reactant 4

HCID 527PropanalHCID 25517Ammonium ChlorideHCID 2872345,6-dihydro-4h-pyrido[3,2,1-jk]carbazol-4-oneHCID 178418339Butyllithium

Product 1

HCID 21252885HCID 21252885, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5,6-dihydro-4H-pyrido[3,2,1-jk]carbazole-4-one (800 mg) prepared by the procedure described in J.O.C., 24, 324 (1959) was dissolved in anhydrous tetrahydrofuran (30 ml). n-butyl lithium (solution in hexane, 3 ml) was added dropwise to the solution cooled in an acetone-dry ice bath, and the mixture was stirred for 30 minutes. Propionaldehyde (0.29 ml) dissolved in anhydrous tetrahydrofuran (15 ml) was gradually added dropwise to the solution cooled in an acetone-dry ice bath, and the mixture was stirred for 90 minutes. Saturated aqueous solution of ammonium chloride of an adequate amount was added to the reaction mixture, and the mixture was heated to room temperature, and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel flash column chromatography (eluent: hexane/ethyl acetate=4:1) to obtain the title compound as a diastereomer (450 mg, 45%).

Workup

  1. temperaturecooled in an acetone-dry ice bath
  2. additionwas gradually added dropwise to the solution
  3. temperaturecooled in an acetone-dry ice bath
  4. stirringthe mixture was stirred for 90 minutes
  5. extractionextracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by silica gel flash column chromatography (eluent: hexane/ethyl acetate=4:1)

Sources & evidence

ORD record
ord-c5a759c9dfa74bb69e9debbe4a0a3a2f
Source dataset
uspto-grants-2000_01
Patent number
US06018046

Reaction notes

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