Hydrochloric Acid → Methyl 2-{[(4-fluorophenyl)methyl]oxy}-5-[(1Z)-3-oxo-1-propen-1-yl]benzoate

HRID 1623740Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][C:10]2[CH:19]=[CH:18][C:17](I)=[CH:16][C:11]=2[C:12]([O:14][CH3:15])=[O:13])=[CH:4][CH:3]=1.C([O:23][CH:24](OCC)[CH:25]=[CH2:26])C.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][C:10]2[CH:19]=[CH:18][C:17](/[CH:26]=[CH:25]\[CH:24]=[O:23])=[CH:16][C:11]=2[C:12]([O:14][CH3:15])=[O:13])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a suspension of methyl 2-{[(4-fluorophenyl)methyl]oxy}-5-iodobenzoate (may be prepared as described in Description 112; 740 mg, 1.92 mmol) in N,N-dimethylformamide (5 ml) was added 3,3-bis(ethyloxy)-1-propene (0.88 ml, 5.8 mmol), potassium carbonate (397 mg, 2.87 mmol) and PdOAc2 (25.8 mg, 0.115 mmol). The reaction was heated in the microwave at 120° C. for 40 minutes, cooled and then 2M HCl (5 ml) was added and the mixture stirred for 20 minutes. The mixture was extracted with diethyl ether (2×10 ml), the organic layer dried (MgSO4), and the solvent removed in vacuo. Purification by column (Si, (solute, 6:1 cyclohexane/ethyl acetate) yielded the title compound. 163 mg.

Workup

temperaturecooled
extractionThe mixture was extracted with diethyl ether (2×10 ml)
dry with materialthe organic layer dried (MgSO4)
customthe solvent removed in vacuo
customPurification by column (Si, (solute, 6:1 cyclohexane/ethyl acetate)

Sources & evidence

ORD record: ord-785011656bdb44bca9a8cb85958264d0
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778939B2

Reaction notes

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