Ethylene Glycol → HCID 55255896, compound

HRID 1615246Notes

Reaction equation

HRID 1615246 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([CH:10]=[O:11])=[CH:6][C:3]=1[C:4]#[N:5].[CH2:12](O)[CH2:13][OH:14].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=O)C>C1(C)C=CC=CC=1>[O:11]1[CH2:12][CH2:13][O:14][CH:10]1[C:7]1[CH:8]=[CH:9][C:2]([F:1])=[C:3]([CH:6]=1)[C:4]#[N:5]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 27695822-Fluoro-5-formylbenzonitrile

Product 1

HCID 55255896HCID 55255896, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2-fluoro-5-formylbenzonitrile (450 mg, 3 mmol) in toluene (10 mL) was added ethylene glycol (2 mL) and p-toluene sulfonic acid (25 mg). The solution was heated to 70° C. overnight. The solution was cooled to room temperature. Ethyl acetate (100 mL) was added and the solution was washed with sat. sodium bicarbonated (10 mL), water (10 mL) and brine (10 mL), dried over MgSO4 and concentrated to a clear oil (567 mg, 98%). 1H NMR (400 MHz, CDCl3) δ 7.78 (dd 1H, J=6.3, 2.3 Hz), 7.74-7.70 (m, 1H), 7.27-7.24 (m, 1H), 5.80 (s, 1H), 4.14-4.08 (m, 4H).

Workup

  1. temperatureThe solution was cooled to room temperature
  2. washthe solution was washed with sat. sodium
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated to a clear oil (567 mg, 98%)

Sources & evidence

ORD record
ord-cf1eca08b081485ca3750ba4e0a5211b
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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