Ethylene Glycol → HCID 54000963, compound

HRID 1934407Notes

Reaction equation

HRID 1934407 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH:5]([C:11]#[N:12])[CH2:6][C:7](=[O:10])[CH2:8][CH3:9])[CH3:2].[CH2:14](O)[CH2:15][OH:16].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>O>[CH2:1]([O:3][C:4](=[O:13])[CH:5]([C:11]#[N:12])[CH2:6][C:7]1([CH2:8][CH3:9])[O:16][CH2:15][CH2:14][O:10]1)[CH3:2]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 241BenzeneHCID 521998p-Toluenesulfonic acid monohydrateHCID 53675399HCID 53675399, compound

Product 1

HCID 54000963HCID 54000963, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 500 mL flask equipped with a reflux condenser and Dean-Stark trap were combined 40.0 g (218 mmol) of 2-cyano-4-oxohexanoic acid ethyl ester, 20.3 g (327 mmol) of ethylene glycol, 0.83 g (4.3 mmol) of p-toluenesulfonic acid monohydrate, and 100 mL of benzene. The reaction was heated to reflux until approximately 4.5 mL of water had been collected in the trap. The reaction was cooled to ambient temperature, washed with 50 mL of water, 50 mL of saturated δsodium bicarbonate solution and dried over sodium sulfate. The mixture was then concentrated to 46.0 g (93%) of α-cyano-2-ethyl-1,3-dioxolane-2-propanoic acid ethyl ester as a light tan oil. An NMR of the crude product showed less than 10% residual ketone remained and the crude product was used without further purification. nmr (500 MHz, CDCl3) δ0.92 (t, J=7.5 Hz, 3H), 1.31 (t, J=7.2 Hz, 3H), 1.64 (q, J=7.5 Hz, 2H), 2.29 (dd, J=6.8, 14.6 Hz, 1H), 2.41 (dd, J=6.3, 14.6 Hz, 1H), 3.59 (dd, J=6.3, 6.8 Hz, 1H), 3.59 (m, 4H), 4.24 (q, J=7.2 Hz, 2H).

Workup

  1. customIn a 500 mL flask equipped with a reflux condenser
  2. temperatureThe reaction was heated
  3. customhad been collected in the trap
  4. washwashed with 50 mL of water, 50 mL of saturated δsodium bicarbonate solution
  5. dry with materialdried over sodium sulfate
  6. concentrationThe mixture was then concentrated to 46.0 g (93%) of α-cyano-2-ethyl-1,3-dioxolane-2-propanoic acid ethyl ester as a light tan oil
  7. customthe crude product was used without further purification

Sources & evidence

ORD record
ord-968c2a834c86439a967a83869bd07250
Source dataset
uspto-grants-2002_05
Patent number
US06384041B1

Reaction notes

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