Ethylene Glycol → HCID 66918225, compound

HRID 746476Notes

Reaction equation

HRID 746476 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([B:9]([OH:11])[OH:10])[CH:6]=[CH:7][CH:8]=1)#[N:2].[CH2:12](O)[CH2:13][OH:14].CCCCCC>C1COCC1>[B:9]([O:11][CH2:12][CH2:13][OH:14])([OH:10])[C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[N:2])[CH:4]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 8058HexaneHCID 27343253-Cyanophenylboronic acid

Product 1

HCID 66918225HCID 66918225, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Cyanophenyl boronic acid (1 g, 6.8 mmol) was dissolved in dry THF (10 mL) under nitrogen. Ethylene glycol (379 μL, 422 mg, 6.8 mmol) was added and the reaction was heated to reflux for 4 hours then cooled to room temperature. THF was removed by rotary evaporator to give a white solid. Cold hexane was added and the product was collected by filtration giving a white solid (1.18 g, quant. yield). 1H-NMR (300.058 MHz, DMSO-d6) δ ppm 7.92-8.01 (3H, m), 7.50-7.64 (1H, m), 4.35 (4H, s)

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 4 hours
  3. customTHF was removed by rotary evaporator
  4. customto give a white solid
  5. filtrationthe product was collected by filtration

Sources & evidence

ORD record
ord-dfeadae968ab48af8fdb475e72afcd17
Source dataset
uspto-grants-2008_07
Patent number
US07393856B2

Reaction notes

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