tert-Butyl 2-(1-ethoxy-2-methyl-1-oxopropan-2-yl)-1H-indole-1-carboxylate → Ethyl 2-(1H-indol-2-yl)-2-methylpropanoate

HRID 1964324Notes

Reaction equation

HRID 1964324 reaction equation
[CH2:1]([O:3][C:4]([C:6]([C:9]1[N:10](C(OC(C)(C)C)=O)[C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)([CH3:8])[CH3:7])=[O:5])[CH3:2]>ClCCl.C(O)(C(F)(F)F)=O>[NH:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:17]=[C:9]1[C:6]([CH3:7])([CH3:8])[C:4]([O:3][CH2:1][CH3:2])=[O:5]

Participants

4

Reactant 1

HCID 53439126tert-Butyl 2-(1-ethoxy-2-methyl-1-oxopropan-2-yl)-1H-indole-1-carboxylate

Product 1

HCID 53438556Ethyl 2-(1H-indol-2-yl)-2-methylpropanoateYield 78.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl 2-(2-(ethoxycarbonyl)propan-2-yl)-1H-indole-1-carboxylate (22.9 g, 69.1 mmol) was dissolved in dichloromethane (200 mL) before TFA (70 mL) was added. The mixture was stirred for 5 h at room temperature. The mixture was evaporated to dryness, taken up in dichloromethane and washed with saturated sodium bicarbonate solution, water, and brine. The product was purified by column chromatography on silica gel (0-20% EtOAc in hexane) to give ethyl 2-(1H-indol-2-yl)-2-methylpropanoate (12.5 g, 78%).

Workup

  1. additionwas added
  2. customThe mixture was evaporated to dryness
  3. washwashed with saturated sodium bicarbonate solution, water, and brine
  4. customThe product was purified by column chromatography on silica gel (0-20% EtOAc in hexane)

Sources & evidence

ORD record
ord-782a121c1cd848cbbe6857d545e87339
Source dataset
uspto-grants-2013_04
Patent number
US08415387B2

Reaction notes

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