Diethyl Ether → [5-(Tert-butyl-dimethyl-silanyloxy)-indol-1-yl]-acetic acid ethyl ester

HRID 915434Notes

Reaction equation

HRID 915434 reaction equation
[C:1]([Si:5]([CH3:17])([CH3:16])[O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[CH:10]2)([CH3:4])([CH3:3])[CH3:2].Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)C>CN(C=O)C>[CH2:23]([O:22][C:20](=[O:21])[CH2:19][N:12]1[C:13]2[C:9](=[CH:8][C:7]([O:6][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:17])[CH3:16])=[CH:15][CH:14]=2)[CH:10]=[CH:11]1)[CH3:24]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 222508175-(tert-Butyldimethylsilyloxy)-1H-indole

Product 1

HCID 68822475[5-(Tert-butyl-dimethyl-silanyloxy)-indol-1-yl]-acetic acid ethyl esterYield 104%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 5-(tert-butyl-dimethyl-silanyloxy)-1H-indole (9.2 g, 37.2 mmol), ethyl bromoacetate (4.79 ml, 40.9 mmol) and cesium carbonate (36.4 g, 111.5 mmol) in DMF (140 ml) was stirred for 3 h at RT. Diethyl ether was added and the mixture was washed with 1N HCl and water, and dried over sodium sulfate. The ether phase was concentrated under reduced pressure to give 12.9 g (quant.) of [5-(tert-butyl-dimethyl-silanyloxy)-indol-1-yl]-acetic acid ethyl ester which was used in the next step without further purification.

Workup

  1. washthe mixture was washed with 1N HCl and water
  2. dry with materialdried over sodium sulfate
  3. concentrationThe ether phase was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8c20dd66e7bf4a8485001374fddb480e
Source dataset
uspto-grants-2007_09
Patent number
US07265149B2

Reaction notes

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