Methyl iodide → (1-Methyl-1H-indol-6-yl)methanol

HRID 378368Notes

Reaction equation

HRID 378368 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][OH:13])[CH:10]=2)[CH:5]=[CH:4]1.[CH3:14]I>CN(C)C=O>[CH3:14][N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:12][OH:13])[CH:10]=2)[CH:5]=[CH:4]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 27734596-Hydroxymethylindole

Product 1

HCID 18673032(1-Methyl-1H-indol-6-yl)methanolYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
0 °C

Procedure

NaH(8.2 mm) in N,N-dimethylformamide ("DMF") (20 mL) was cooled to 0° C., then treated with a solution of the known 1H-indole-6-methanol (1 g,6.8 mm) in DMF(8 mL). After stirring for 1 hour at 0° C., methyl iodide ("MeI") (0.51 mL, 8.2 mm) dissolved in DMF (2 mL) was added, and the mixture was stirred at 0° C. overnight, then poured into ice/H2O(250 ml) and extracted with EtOAc(50 mL×3). The organic fraction was dried over MgSO4, filtered, evaporated and purified by flash column chromatography to afford 1-methyl-1H-indole-6-methanol (0.82 g. 75%). This product (1-methyl-1H-indole-6-methanol, 1 g, 6.2 mm) was dissolved in a mixture of pyridine (5 mL) and acetic anhydride (Ac2O) (5 mL) and stirred at room temperature overnight. The solvent was evaporated, and the residue purified by flash column chromatography to afford 1.09 g of Acetic acid 1-methyl-1H-indol-6-yl methyl ester.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at 0° C. overnight
  3. extractionextracted with EtOAc(50 mL×3)
  4. dry with materialThe organic fraction was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-707a1220dfcf4d82a55a6079f14296b7
Source dataset
uspto-grants-2000_02
Patent number
US06030994

Reaction notes

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