Methanol → Indole

HRID 378373Notes

Reaction equation

HRID 378373 reaction equation
C([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][N:11]2C(C)C)=[CH:7][CH:6]=1)(OC)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].CO.[OH-].[Na+]>O1CCCC1>[NH:11]1[C:12]2[C:8](=[CH:7][CH:6]=[CH:5][CH:13]=2)[CH:9]=[CH:10]1

Participants

6

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 10608809Methyl 1-isopropyl-1H-indole-6-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 798IndoleYield 158.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of 0.250 g (1.15 mmole) of 6-carbomethoxy-1-(2-propyl)indole in 2 mL of anhydrous tetrahydrofuran was added dropwise to a stirring slurry of lithium aluminum hydride (52.4 ing 1.38 mmole) in 7 mL of anhydrous tetrahydrofuran under argon it 0° C. and then stirred at 25° C. for 45 min. The solution was cooled to 0° C. and 0.340 mL of methanol was added dropwise, followed by 0.58 mL of 1N sodium hydroxide solution. The slurry was stirred at 25° C. for 15 min. The white precipitate was filtered through celite, and the solution concentrated. The residue was suspended in 20 mL of ethyl acetate and 20 mL of water. The layers were separated. The aqueous layer was back-extracted with ethyl acetate and both ethyl acetate layers were combined and dried over magnesium sulfate. Concentration gave 6-hydroxymethyl-1-(2-prol:)yl)indole as an oil (214 mg).

Workup

  1. temperatureThe solution was cooled to 0° C.
  2. stirringThe slurry was stirred at 25° C. for 15 min
  3. filtrationThe white precipitate was filtered through celite
  4. concentrationthe solution concentrated
  5. customThe layers were separated
  6. extractionThe aqueous layer was back-extracted with ethyl acetate
  7. dry with materialdried over magnesium sulfate
  8. concentrationConcentration

Sources & evidence

ORD record
ord-d144c4414f02400480ba31b4c2f967ad
Source dataset
uspto-grants-2000_02
Patent number
US06030994

Reaction notes

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