Diethyl Carbonate → HCID 89524881, compound

HRID 1620988Notes

Reaction equation

HRID 1620988 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([CH2:13][OH:14])([CH2:11]O)[CH2:9][OH:10])[CH:5]=[CH:6][CH:7]=1.C(=O)(OCC)OCC.[OH-].[K+]>CCO>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2([CH2:9][OH:10])[CH2:11][O:14][CH2:13]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7766Diethyl CarbonateHCID 14797Potassium HydroxideHCID 89526095HCID 89526095, compound

Product 1

HCID 89524881HCID 89524881, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
190 °C

Procedure

A mixture of Example 86C (1.1 g, 5.10 mmol), diethyl carbonate (722 mg, 6.10 mmol), and KOH (15 mg) was heated at 80° C., allowing the mixture to become homogeneous. The mixture was then heated at 95° C. for 4 hours during which time EtOH distilled off from the mixture. Distillation was continued until the pot temperature was 190° C., and then the pressure was reduced to 50 mm, maintaining the pot temperature at 190° C. for 1 hour. The residue was purified by Prep-TLC (eluted with petroleum ether:ethyl acetate=1:1).

Workup

  1. distillationdistilled off from the mixture
  2. distillationDistillation
  3. customwas 190° C.
  4. customThe residue was purified by Prep-TLC (eluted with petroleum ether:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-a5e520c82354461d96dfb11e558ff3d3
Source dataset
uspto-grants-2014_07
Patent number
US08772500B2

Reaction notes

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