Ethylene Glycol → HCID 59300654, compound

HRID 1675268Notes

Reaction equation

HRID 1675268 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[F:10][C:11]([F:20])([F:19])[C:12]1[CH:17]=[CH:16][C:15]([SH:18])=[CH:14][CH:13]=1.C(O)CO.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl.[Cu]I.C(O)(C)C>[F:20][C:11]([F:10])([F:19])[C:12]1[CH:13]=[CH:14][C:15]([S:18][C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=2)[CH:5]=[O:6])=[CH:16][CH:17]=1

Participants

8

Reactant 4

HCID 174Ethylene GlycolHCID 11430Potassium CarbonateHCID 1366534-(Trifluoromethyl)thiophenolHCID 2526103-Iodobenzaldehyde

Product 1

HCID 59300654HCID 59300654, compoundYield 44.5%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
85 °C

Procedure

To a sealed tube flushed with nitrogen, was added 3-iodobenzaldehyde 31.1 (300 mg, 1.29 mmol), 4-(trifluoromethyl)benzenethiol (230 mg, 1.29 mmol), copper (I) iodide (24.6 mg, 0.129 mmol), ethylene glycol (0.144 mL, 2.59 mmol), potassium carbonate (357 mg, 2.59 mmol), and isopropanol (6.50 mL). The reaction mixture was heated at 85° C. for 48 hours. The reaction was then cooled and diluted with DCM and filtered over a pad of diatomaceous earth. The filtrate was concentrated, and the residue was purified by medium pressure chromatography (silica gel, 0 to 20% diethyl ether:hexanes) to give 31.2 (162 mg). 1H NMR (400 MHz, CDCl3) δ ppm 9.92 (1 H, s), 7.85 (1 H, s), 7.77 (1 H, d, J=7.4 Hz), 7.59 (1 H, d, J=7.8 Hz), 7.44-7.50 (3 H, m), 7.29 (2 H, d, J=8.2 Hz).

Workup

  1. customTo a sealed tube flushed with nitrogen
  2. temperatureThe reaction was then cooled
  3. filtrationfiltered over a pad of diatomaceous earth
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by medium pressure chromatography (silica gel, 0 to 20% diethyl ether:hexanes)

Sources & evidence

ORD record
ord-76609171461b49a68bf1cb350d681db0
Source dataset
uspto-grants-2011_08
Patent number
US08003648B2

Reaction notes

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