Water → 1-methyl-1H-indole-5-carbaldehyde

HRID 40582

Reaction equation

HRID 40582 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.N12CCN(CC1)C[CH2:13]2.CCOC(C)=O.O>C(=O)(OC)OC>[CH3:13][N:1]1[C:9]2[C:4](=[CH:5][C:6]([CH:10]=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 9237DabcoHCID 589040Indole-5-carboxaldehyde

Product 1

HCID 75375341-methyl-1H-indole-5-carbaldehydeYield 46%

Reagents, catalysts & solvents 1

HCID 12021Dimethyl CarbonateSolvent

Conditions

Temperature
90 °C

Procedure

A solution of indole-5-carbaldehyde (0.5 g) in dimethyl carbonate (5 mL) was treated with 1,4-diaza-bicyclo[2.2.2]octane (38 mg). The resulting mixture was heated to 90° C. for 5 h and cooled to room temperature (rt). EtOAc (10 mL) and water (10 mL) were added, and the aqueous phase was extracted with EtOAc (3×10 mL). The combined organic extracts were washed with brine (1×20 mL), dried (MgSO4), and concentrated. Chromatography of the residue (0-50% EtOAc-hexanes) gave the title compound as a white solid (46%).

Workup

  1. temperaturecooled to room temperature (rt)
  2. extractionthe aqueous phase was extracted with EtOAc (3×10 mL)
  3. washThe combined organic extracts were washed with brine (1×20 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fa0519e4d41b43b5a7f430548df2fe8e
Source dataset
uspto-grants-2013_09
Patent number
US08530476B2

Linked notes

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