Carbonic acid, bis(1,1-dimethylethyl) ester → tert-Butyl 2-(2-ethoxy-2-oxoethyl)-1H-indole-1-carboxylate

HRID 1847771Notes

Reaction equation

HRID 1847771 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].[C:16](=O)([O:22]C(C)(C)C)[O:17][C:18]([CH3:21])([CH3:20])[CH3:19]>ClCCl.CN(C)C1C=CN=CC=1>[CH2:14]([O:13][C:11]([CH2:10][C:2]1[N:1]([C:16]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:22])[C:9]2[C:4]([CH:3]=1)=[CH:5][CH:6]=[CH:7][CH:8]=2)=[O:12])[CH3:15]

Participants

5

Reactant 2

HCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 11106442Ethyl 2-(1H-indol-2-yl)acetate

Product 1

HCID 53419936tert-Butyl 2-(2-ethoxy-2-oxoethyl)-1H-indole-1-carboxylateYield 91.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of ethyl 2-(1H-indol-2-yl)acetate (14.7 g, 72.2 mmol) in dichloromethane (150 mL) was added 4-dimethylaminopyridine (8.83 g, 72.2 mmol) and di-tert-butyl carbonate (23.7 g, 108 mmol) in portions. After stirring for 2 h at room temperature, the mixture was diluted with dichloromethane, washed with water, dried over magnesium sulfate and purified by silica gel chromatography (0 to 20% EtOAc in hexane) to give tert-butyl 2-((ethoxycarbonyl)methyl)-1H-indole-1-carboxylate (20.0 g, 91%).

Workup

  1. washwashed with water
  2. dry with materialdried over magnesium sulfate
  3. custompurified by silica gel chromatography (0 to 20% EtOAc in hexane)

Sources & evidence

ORD record
ord-8635a9e186d44de89f008a6d50a60b9d
Source dataset
uspto-grants-2015_02
Patent number
US08952049B2

Reaction notes

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