Ethanol → ethyl 2-(5-methoxy-1H-indol-3-yl)-2-oxoacetate

HRID 624043Notes

Reaction equation

HRID 624043 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[C:12](=[O:16])[C:13](Cl)=[O:14].CCN(CC)CC.[CH2:24]([OH:26])[CH3:25]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[C:12](=[O:16])[C:13]([O:26][CH2:24][CH3:25])=[O:14]

Participants

4

Reactant 3

HCID 702EthanolHCID 8471TriethylamineHCID 9991766HCID 9991766, compound

Product 1

HCID 2763354ethyl 2-(5-methoxy-1H-indol-3-yl)-2-oxoacetate

Procedure

To a solution 2-(5-methoxy-1H-indol-3-yl)-2-oxoacetyl chloride (14.78 g, 62.20 mmol) in ethanol (144 mL), Et3N (10.40 mL, 74.63 mmol) was added at 0° C. and the resulting yellow suspension was stirred at rt for 1 h. The percipitate was filtered off, washed with cold ethanol and diethylether to yield ethyl 2-(5-methoxy-1H-indol-3-yl)-2-oxoacetate as an orange oil. LC-MS conditions B: tR=0.63 min, [M+H]+=248.13.

Workup

  1. filtrationThe percipitate was filtered off
  2. washwashed with cold ethanol and diethylether

Sources & evidence

ORD record
ord-dcb8ba21a0024d29a3ea987764069aaf
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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