Butanal → HCID 19610404, compound

HRID 1602109Notes

Reaction equation

HRID 1602109 reaction equation
[OH-].[K+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]1[CH:12]=O.[CH:14](=[O:18])[CH2:15][CH2:16][CH3:17].C(OC(C)C)(C)C>O.CCO>[CH2:16](/[C:15](=[CH:12]\[C:4]1[NH:3][C:11]2[C:6]([CH:5]=1)=[CH:7][CH:8]=[CH:9][CH:10]=2)/[CH:14]=[O:18])[CH3:17]

Participants

7

Reactant 4

HCID 261ButanalHCID 7914Diisopropyl EtherHCID 14797Potassium HydroxideHCID 96389Indole-2-carboxaldehyde

Product 1

HCID 19610404HCID 19610404, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of KOH pellets (0.4 g, 7.1 mmol) in H2O (5 ml), indole-2-carboxaldehyde (0.5 g, 3.44 mmol) in EtOH (45 ml) was added. After cooling to 0° C. butyraldehyde (0.31 ml, 3.44 mmol) was added and the reaction mixture was stirred at room temperature for 12 h. The ethanol was removed under vacuum and the aqueous solution was adjusted to pH 5 and extracted with EtOAc (3×10 ml). The combined organic layers were washed with brine (10 ml), dried over Na2SO4 and evaporated under vacuum. The residue was purified by flash-chromatography (hexane/EtOAc 7:3) to afford, after trituration with isopropyl ether, 0.3 g (44%) of the title compound.

Workup

  1. additionwas added
  2. customThe ethanol was removed under vacuum
  3. extractionextracted with EtOAc (3×10 ml)
  4. washThe combined organic layers were washed with brine (10 ml)
  5. dry with materialdried over Na2SO4
  6. customevaporated under vacuum
  7. customThe residue was purified by flash-chromatography (hexane/EtOAc 7:3)
  8. customto afford

Sources & evidence

ORD record
ord-d38154107c59484f9425a2b0937e044d
Source dataset
uspto-grants-1999_11
Patent number
US05981525

Reaction notes

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