Epichlorohydrin → 4-(oxiran-2-ylmethoxy)-1H-indole
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+].[CH2:13]([CH:15]1[O:17][CH2:16]1)Cl>CS(C)=O.[NH4+].[Cl-]>[NH:6]1[C:7]2[C:3](=[C:2]([O:1][CH2:13][CH:15]3[O:17][CH2:16]3)[CH:10]=[CH:9][CH:8]=2)[CH:4]=[CH:5]1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 45 °C
Procedure
To a solution of 4-hydroxyindole (0.50 g, 3.8 mmol) in dimethylsulfoxide (10 mL) at 45° C. were added potassium hydroxide (0.43 g, 7.6 mmol) and then epichlorohydrin (1.4 g, 15.2 mmol). After being stirred at 45° C. for 4 h, the reaction mixture was diluted with a saturated solution of NH4Cl and extracted with diethyl ether (3×50 mL). The combined organic layers were dried with Na2SO4, and concentrated. The residue was purified by column chromatography on silica gel with benzene/acetone mixtures to give the glycidyl 4-indolyl ether (compound 1a) (0.75 g, quant) as a colorless oil. See FIG. 18.
Workup
- extractionextracted with diethyl ether (3×50 mL)
- dry with materialThe combined organic layers were dried with Na2SO4
- concentrationconcentrated
- customThe residue was purified by column chromatography on silica gel with benzene/acetone
Sources & evidence
- ORD record
- ord-afc273eb32e1489ab3513f59046da63f
- Source dataset
- uspto-grants-2008_11
- Patent number
- US07449480B2
Reaction notes
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