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

HRID 1599910Notes

Reaction equation

HRID 1599910 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 (1.6 M 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 HCI, 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.

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-589e0c1e4e894505bacb6e98999745a7
Source dataset
uspto-grants-1998_04
Patent number
US05741796

Reaction notes

Loading…