Ammonium Chloride → HCID 61262331, compound

HRID 2091013Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]2[CH:7]=[C:8]([C:10]#N)[O:9][C:5]=2[CH:4]=1.[O:14]1CCCC1.[CH:19]1([Mg]Br)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.[Cl-].[NH4+]>O1CCCC1>[CH:19]1([C:10]([C:8]2[O:9][C:5]3[CH:4]=[C:3]([O:2][CH3:1])[CH:13]=[CH:12][C:6]=3[CH:7]=2)=[O:14])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution (20 mL) of 6-methoxy-1-benzofuran-2-carbonitrile (1.00 g) synthesized above in tetrahydrofuran was added 1.0M cyclohexylmagnesium bromide tetrahydrofuran solution (11.5 mL), and the mixture was stirred at 50° C. overnight, and stirred with heating under reflux for 1 hr. Saturated aqueous ammonium chloride solution was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9, volume ratio) to give the title object compound (584 mg, 39%) as a yellow solid.

Workup

stirringstirred
temperaturewith heating
temperatureunder reflux for 1 hr
customto quench
customthe reaction
extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with saturated brine
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9, volume ratio)

Sources & evidence

ORD record: ord-20e55043b3c44204b8afa7b45825271f
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436043B2

Reaction notes

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