Ammonium Chloride → HCID 66777987, compound

HRID 2091171Notes

Reaction equation

[Br:1][C:2]1[C:6]2[CH:7]=[C:8]([O:11][CH3:12])[CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[CH:13]=[O:14].[CH:15]1([Mg]Br)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.[Cl-].[NH4+]>O1CCCC1>[Br:1][C:2]1[C:6]2[CH:7]=[C:8]([O:11][CH3:12])[CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[CH:13]([CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)[OH:14]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution (50 mL) of 3-bromo-5-methoxy-1-benzofuran-2-carbaldehyde (2.26 g) synthesized above in tetrahydrofuran was added a 1.0M solution (13.3 mL) of cyclohexylmagnesium bromide in tetrahydrofuran at −78° C., and the mixture was stirred at −78° C. for 30 min then at 0° C. for 1 hr. Saturated aqueous ammonium chloride solution was added to quench the reaction, tetrahydrofuran was evaporated in an evaporator, and the residue 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 (20% ethyl acetate/hexane) to give the title object compound (1.82 g, 67%) as a yellow oil.

Workup

waitat 0° C. for 1 hr
customto quench
customthe reaction, tetrahydrofuran
customwas evaporated in an evaporator
extractionthe residue 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 (20% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-cc286d41b4ac4055a3e9bd20241f7127
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436043B2

Reaction notes

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