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

HRID 1277246Notes

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-trifluoromethanesulfonyloxybenzoate (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 acetate/hexane 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 acetate/hexane

Sources & evidence

ORD record: ord-b1fe81d58e1d4b9f903dde2d33984fff
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06166006

Reaction notes

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