Methyl iodide → Methyl alpha,1-dimethyl-1H-indole-3-acetate

HRID 1288650Notes

Reaction equation

HRID 1288650 reaction equation
[CH:1]([N-]C(C)C)(C)C.[Li+].[CH3:9][N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:11]1.CI.[Cl-].[NH4+]>O1CCCC1>[CH3:1][CH:19]([C:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:10]([CH3:9])[CH:11]=1)[C:20]([O:22][CH3:23])=[O:21]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamide2×HCID 11106438Methyl 2-(1-methyl-1H-indol-3-yl)acetate

Product 1

HCID 11117483Methyl alpha,1-dimethyl-1H-indole-3-acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of lithium diisopropyl amide, LDA, (5.5 millimole) in 10 mL of dry tetrahydrofuran at -78° C. was added dropwise a solution of methyl 2-(1-methyl-3-indolyl)acetate (1.02 g) in 3 mL of dry tetrahydrofuran. This mixture was stirred for one hour, then 1.42 g of methyl iodide was added and the mixture was warmed to room temperature and stirred for an additional 30 minutes. The mixture was poured into a solution of aqueous saturated ammonium chloride and then extracted with diethyl ether. The ether extract was dried over magnesium sulfate and concentrated to an oil by evaporation. The residue was subjected to silica gel chromatography using a developing solution of hexanes/ethyl acetate (6:1 by volume) to give 1.04 g of the product.

Workup

  1. stirringstirred for an additional 30 minutes
  2. extractionextracted with diethyl ether
  3. extractionThe ether extract
  4. dry with materialwas dried over magnesium sulfate
  5. concentrationconcentrated to an oil by evaporation

Sources & evidence

ORD record
ord-3e291ae7368a4eec8cdb440f682a0af6
Source dataset
uspto-grants-1998_05
Patent number
US05747236

Reaction notes

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