2-Methylindole → Ethyl 2-(1H-indol-2-yl)acetate

HRID 583657Notes

Reaction equation

HRID 583657 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]CCCC.CC([O-])(C)C.[K+].[CH2:22]([O:24][C:25](=O)[O:26]CC)[CH3:23]>CCOCC>[NH:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[C:2]1[CH2:1][C:25]([O:24][CH2:22][CH3:23])=[O:26]

Participants

6

Reactant 4

HCID 72242-MethylindoleHCID 7766Diethyl CarbonateHCID 23665647Potassium tert-butoxideHCID 178418339Butyllithium

Product 1

HCID 11106442Ethyl 2-(1H-indol-2-yl)acetate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2-Methylindole (1.7 g, 13 mmol) in 130 mL Et2O was treated with nBuLi (1.6M in hexane, 24.4 mL, 39 mmol) and KOtBu (1.0M in THF, 26 mL, 26 mmol) at RT for 40 min, then diethylcarbonate (3.15 mL, 26 mmol) was added. After 1 h the reaction was quenched with water, adjusted to pH 7 with 6N HCl, extracted with EtOAc, then the organic layer was washed with water and brine, dried (MgSO4), and concentrated. Flash chromatography (silica 10% then 20% EtOAc/hexane) provided 4-1 as a brown oil. Rf 0.33 (silica, 20% EtOAc/hexane).

Workup

  1. customAfter 1 h the reaction was quenched with water
  2. extractionextracted with EtOAc
  3. washthe organic layer was washed with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a9793c433acf447399890b75e8711729
Source dataset
uspto-grants-1999_07
Patent number
US05929120

Reaction notes

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