Potassium Carbonate → HCID 118452447, compound

HRID 1773236Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:15](=O)[C:16]([F:19])([F:18])[F:17])=[C:6]([CH:14]=1)[O:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10].C([O-])([O-])=O.[K+].[K+]>CC#N>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[C:15]([C:16]([F:19])([F:18])[F:17])=[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[O:7][C:6]=2[CH:14]=1

Participants

Conditions

Temperature: 90 °C

Procedure

The mixture of ethyl 2-(5-methyl-2-(2,2,2-trifluoroacetyl)phenoxy)acetate (7.3 g, 25.2 mmol) and pre-oven dried K2CO3 (5.21 g, 37.7 mmol) in 25 mL of CH3CN in sealed tube was heated and stirred at 90° C. for two days. After cooling to room temperature, the reaction was filtered, and the solid was washed with anhydrous CH3CN. The combined filtrate was concentrated to dryness under reduced pressure. The resulting residue was purified by silica gel flash chromatography, 100% Heptane-2% Ethyl Acetate/98% Heptane, to give ethyl 6-methyl-3-(trifluoromethyl)benzofuran-2-carboxylate (2.35 g). LCMS retention time=1.52 minutes (LC method 1); MS (m+1)=273.3. 1H NMR (400 MHz, CHLOROFORM-d) δ 1.45 (t, J=7.1 Hz, 3H), 2.53 (s, 3H), 4.50 (q, J=7.2 Hz, 2H), 7.24 (dd, J=8.3, 0.9 Hz, 1H), 7.43 (d, J=0.6 Hz, 1H), 7.69-7.77 (m, 1H).

Workup

temperaturewas heated
temperatureAfter cooling to room temperature
filtrationthe reaction was filtered
washthe solid was washed with anhydrous CH3CN
concentrationThe combined filtrate was concentrated to dryness under reduced pressure
customThe resulting residue was purified by silica gel flash chromatography, 100% Heptane-2% Ethyl Acetate/98% Heptane

Sources & evidence

ORD record: ord-240a5fd0a28941789d6f98ddd19913c3
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09255093B2

Reaction notes

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