Reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[OH-].[K+].CS(C)=O.Br[C:18]([CH3:25])([CH3:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20]>O>[CH2:22]([O:21][C:19](=[O:20])[C:18]([O:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2)([CH3:25])[CH3:24])[CH3:23]Participants
Procedure
A mixture of 4-hydroxyindole (0.100 g, 0.75 mmol, 1.0 eq), powdered potassium hydroxide (0.046 g, 0.83 mmol, 1.1 eq), and DMSO (2 mL) was stirred at room temperature for 1 hour and then ethyl 2-bromo-2-methylpropionate (0.161 g, 0.12 mL, 0.83 mmol, 1.1 eq) was added to the above mixture dropwise. The reaction mixture was stirred at room temperature for another 2 hours before 15 mL of water was added. The mixture was extracted with ethyl acetate (2×30 mL). The organic layer was collected, combined, washed with water (6×25 mL) and brine (2×20 mL), and dried over anhydrous Na2SO4. The solvent was removed in vacuo. The residue thus obtained was purified by flash chromatograph over silica gel using hexane/ethyl acetate (95/5) as an eluant to afford 2-(1H-indol-4-yloxy)-2-methylpropionic acid ethyl ester (0.144 g, yield: 80%).
Workup
- additionwas added
- extractionThe mixture was extracted with ethyl acetate (2×30 mL)
- customThe organic layer was collected
- washwashed with water (6×25 mL) and brine (2×20 mL)
- dry with materialdried over anhydrous Na2SO4
- customThe solvent was removed in vacuo
- customThe residue thus obtained
- customwas purified by flash chromatograph over silica gel
Sources & evidence
- ORD record
- ord-58d279f79cc441aba22cf387d8ad64c4
- Source dataset
- uspto-grants-2008_11
- Patent number
- US07449478B2
Linked notes
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