Propionyl chloride → HCID 19808783, compound

HRID 374007Notes

Reaction equation

HRID 374007 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][O:13][CH3:14])[CH:7]=[CH:6]2.CCCCCC.C([Li])CCC.[C:26](Cl)(=[O:29])[CH2:27][CH3:28].C(=O)([O-])O.[Na+]>O1CCCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][O:13][CH3:14])[C:7]([C:26](=[O:29])[CH2:27][CH3:28])=[CH:6]2

Participants

7

Reactant 4

HCID 62324Propionyl chlorideHCID 516892Sodium BicarbonateHCID 19808808HCID 19808808, compoundHCID 178418244HCID 178418244, compound

Product 1

HCID 19808783HCID 19808783, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-30 °C

Procedure

3.00 g of 5-methoxy-1-methoxymethylindole was dissolved in 15 ml of anhydrous tetrahydrofuran. Thereto was dropwise added 11.0 ml of 1.5 M n-butyllithium hexane solution, in 5 minutes with stirring at -30° C. The resulting mixture was stirred at 0° C. for 30 minutes. This solution was dropwise added to a solution of 1.59 g of propionyl chloride dissolved in 15 ml of anhydrous tetrahydrofuran, in 30 minutes with stirring at -60° C. The reaction mixture was stirred at room temperature for 10 minutes, and then was added to 50 ml of an aqueous saturated sodium hydrogencarbonate solution in one portion. Thereto was added 150 ml of ethyl acetate. The organic layer was separated, washed with an aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography (eluant: toluene/ethyl acetate=50/1) to obtain 1.34 g (yield: 35%) of 5-methoxy-1-methoxymethyl-2-propionylindole as a light yellow oily material.

Workup

  1. stirringThe resulting mixture was stirred at 0° C. for 30 minutes
  2. stirringwith stirring at -60° C
  3. stirringThe reaction mixture was stirred at room temperature for 10 minutes
  4. customThe organic layer was separated
  5. washwashed with an aqueous saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed by distillation under reduced pressure
  8. customThe residue was purified by column chromatography (eluant: toluene/ethyl acetate=50/1)

Sources & evidence

ORD record
ord-a10a17ecde5a46e099259721299bde56
Source dataset
uspto-grants-1992_11
Patent number
US05166204

Reaction notes

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