Diethyl Ether → 1-(7-ethyl-1H-indol-3-yl)-3-phenylpropanone

HRID 652366Notes

Reaction equation

C([Mg]Br)C.[CH2:5]([C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:15]=1[NH:14][CH:13]=[CH:12]2)[CH3:6].[C:16](Cl)(=O)[CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Cl-].[NH4+].CC[O:31]CC>C1C=CC=CC=1>[CH2:5]([C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:15]=1[NH:14][CH:13]=[C:12]2[CH2:16][C:17](=[O:31])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH3:6]

Participants

Conditions

Temperature: -10 °C

Procedure

To a vigorously stirred solution of ethyl magnesium bromide (2.85M in ether, 0.07 mol, 24.6 mL) in anhydrous ether (50 mL), was added a solution of 7-ethyl-1H-indole (7.25 g, 0.05 mol) in benzene (25 mL), dropwise over the course of 10 minutes. The resulting pale green mixture was heated at reflux for 2 hours, and then cooled to -10° C. with a dry ice/methanol bath. A solution of hydrocinnamoyl chloride (8.43 g, 0.05 mol) in benzene (20 mL) was added dropwise (45 minutes). The reaction mixture was allowed to warm to room temperature; after an additional 2 hours, no starting material was detected by TLC analysis. Aqueous ammonium chloride (10%, 30 mL) was added to the reaction mixture and a white precipitate formed, which was collected by filtration, washed with ether, and dried in vacuo to yield 7.78 g (56%) of the desired ketone, m.p. 140°-141.5° C.

Workup

customdropwise over the course of 10 minutes
temperatureThe resulting pale green mixture was heated
temperatureat reflux for 2 hours
temperatureto warm to room temperature
customa white precipitate formed
filtrationwhich was collected by filtration
washwashed with ether
customdried in vacuo

Sources & evidence

ORD record: ord-154a13be251e4175844176496720bd44
Source dataset: uspto-grants-1987_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04670462

Reaction notes

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