Hydrochloric Acid → HCID 62800977, compound

HRID 1179123Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[O:10][CH3:11].II.Cl[CH:15]1[CH2:19][CH2:18][CH2:17][C:16]1=[O:20].Cl>C1COCC1.CCOCC>[CH3:11][O:10][C:3]1[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=1[CH:15]1[CH2:19][CH2:18][CH2:17][C:16]1=[O:20]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 1-bromo-2,4-dimethoxybenzene (345 μL, 1.2 eq.) in dry THF (0.5 mL) was added dropwise, under N2, to a suspension of Mg turnings (64 mg, 1.3 eq.) in dry THF (0.7 mL) and in presence of a catalitic amount of I2. The reaction mixture was stirred at reflux for 1 hr and then cooled down to 0° C. To this mixture was added dropwise a solution of 2-chlorocyclopentanone (0.2 mL, 2 mmol) in anh. THF (0.5 mL) and the reaction mixture was heated to reflux for 2 hr. The mixture was allowed to cool at r.t., it was diluted with Et2O and slowly mixed with ice and 1M HCl. The organic layer was then separated, washed twice with brine and dried over anh. Na2SO4. The solids were filtered and the solvent evaporated. The crude red oil was purified by flash chromatography (silica gel, cHex/EtOAc 8:2) to give the title compound (297 mg, 67%) as a yellow oil.

Workup

temperatureat reflux for 1 hr
temperaturethe reaction mixture was heated
temperatureto reflux for 2 hr
temperatureto cool at r.t.
customThe organic layer was then separated
washwashed twice with brine
dry with materialdried over anh. Na2SO4
filtrationThe solids were filtered
customthe solvent evaporated
customThe crude red oil was purified by flash chromatography (silica gel, cHex/EtOAc 8:2)

Sources & evidence

ORD record: ord-5ff0384b7a7a4d6eb66c3c1d8dc3706f
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07279474B2

Reaction notes

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