Water → Ethyl 3-methoxy-4-[2-(4-methylphenyl)ethynyl]-benzoate

HRID 1388002Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1OS(C(F)(F)F)(=O)=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7].[CH3:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]#[CH:30])=[CH:25][CH:24]=1.C(N(CC)CC)C.O>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[C:30]#[C:29][C:26]1[CH:27]=[CH:28][C:23]([CH3:22])=[CH:24][CH:25]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of ethyl 3-methoxy-4-trifluoromethane-sulfonyloxybenzoate (3.95 g), 4-methylphenylacetylene (1.54 g) and triethylamine (5.0 ml) in DMF (40 ml) was added bistriphenylphosphine palladium dichloride (0.25 g), and the mixture was stirred at 100° C. for 3 hours and then cooled to room temperature. To the mixture was added water, and the mixture was extracted with diethylether. The organic layer was washed with saturated brine and dried with magnesium sulfate. Under reduced pressure, the mixture was concentrated, and the residue was purified with column chromatography (ethyl acetate/hexane=1:9) and recrystallized from ethyl acetateihexane to give pale yellow crystals of ethyl 3-methoxy-4-[2-(4-methylphenyl)ethynyl]-benzoate (2.02 g).

Workup

temperaturecooled to room temperature
extractionthe mixture was extracted with diethylether
washThe organic layer was washed with saturated brine
dry with materialdried with magnesium sulfate
concentrationUnder reduced pressure, the mixture was concentrated
customthe residue was purified with column chromatography (ethyl acetate/hexane=1:9)
customrecrystallized from ethyl acetateihexane

Sources & evidence

ORD record: ord-d5b760f78b1541f6ad745dcc1df15c0d
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06268354B1

Reaction notes

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