Methyl iodide → 2-ethyl-1H-indole

HRID 589353Notes

Reaction equation

HRID 589353 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[Li][CH2:12]CCC.C(O)(C)(C)C.IC>O.C(OCC)C>[CH2:1]([C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH3:12]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 6386tert-ButanolHCID 72242-MethylindoleHCID 178418339Butyllithium

Product 1

HCID 38016182-ethyl-1H-indoleYield 67.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

In an ice water bath, 2-methylindole (5 g, 38.1 mmol), 300 mL anhydrous diethyl ether, 2.4 M n-BuLi 47.5 mL (114 mmol), tert-butanol (8.5 g, 75.8 mmol) were added into a reaction vessel. Upon completion of addition, under protection of nitrogen, the reaction was stirred at room temperature for 0.5 h. Then the system was cooled to −70° C., and iodomethane (10.245 g, 72.2 mmol) was added dropwise. Upon completion of addition, it was reacted for 2 h maintaining this temperature. Then it was warmed up to −40° C. 2 mL water was added, and then warmed up to room temperature. The system was poured into water, adjusted to pH=6, extracted with diethyl ether, dried and rotate evaporated to dryness to obtain the product 3.74 g, at a yield of 67.7%.

Workup

  1. additionUpon completion of addition
  2. temperatureThen the system was cooled to −70° C.
  3. additionUpon completion of addition, it
  4. customwas reacted for 2 h
  5. temperaturemaintaining this temperature
  6. temperatureThen it was warmed up to −40° C
  7. temperaturewarmed up to room temperature
  8. extractionextracted with diethyl ether
  9. customdried
  10. customrotate evaporated to dryness

Sources & evidence

ORD record
ord-3716dc400ca24c4e80de6e2bb99fcbb7
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

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