Diethyl Ether → 1-(1-Benzyl-1H-indol-4-yl)ethan-1-one
Reaction equation
[CH3:1][Mg]I.[CH2:4]([N:11]1[C:19]2[C:14](=C(C#N)[CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[Cl-].[NH4+].C([O:26][CH2:27][CH3:28])C>O1CCCC1>[C:27]([C:28]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:14]=1[CH:13]=[CH:12][N:11]2[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[O:26])[CH3:1]Participants
Procedure
3.3 ml of a 2M solution of methylmagnesium iodide in diethyl ether was added to a mixture of 1.00 g of 1-benzyl-4-cyanoindole (prepared as described in Example 88) in 50 ml of tetrahydrofuran, with ice-cooling, and the reaction mixture was stirred for 1 hour. After this time, a saturated aqueous solution of ammonium chloride was added to the reaction mixture. The aqueous layer was extracted with diethyl ether, and the resulting organic fraction was washed with water, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The resulting residue was purified by silica gel column chromatography, using 50 g of silica gel and a 4:1 v/v mixture of hexane and ethyl acetate as the eluent, to yield 1.00 g of the title compound as an oil.
Workup
- temperaturecooling
- extractionThe aqueous layer was extracted with diethyl ether
- washthe resulting organic fraction was washed with water
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated by evaporation under reduced pressure
- customThe resulting residue was purified by silica gel column chromatography
- additiona 4:1 v/v mixture of hexane and ethyl acetate as the eluent
Sources & evidence
- ORD record
- ord-a00412a7d9f141e2ab3ffb4f0a258e9c
- Source dataset
- uspto-grants-1999_03
- Patent number
- US05877199
Reaction notes
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