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

HRID 342061Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:10][OH:11])[CH:8]=2)[CH:3]=[CH:2]1.[CH3:12]I>CN(C)C=O>[CH3:12][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:10][OH:11])[CH:8]=2)[CH:3]=[CH:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

NaH(8.2mm) 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

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

Sources & evidence

ORD record: ord-b4940309b8ee42f3b006784355b69149
Source dataset: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05856517

Reaction notes

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