Methanol → HCID 67520042, compound

HRID 1925618Notes

Reaction equation

HRID 1925618 reaction equation
[C:1]1(=O)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[N:11](C(OC)OC)C.[C:18]([CH2:20][C:21]([O:23][CH3:24])=[O:22])#N.[CH3:25][OH:26]>>[O:26]=[C:25]1[NH:11][C:2]2[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:1]=2[CH:18]=[C:20]1[C:21]([O:23][CH3:24])=[O:22]

Participants

5

Reactant 4

HCID 887MethanolHCID 7747Methyl cyanoacetateHCID 10403CyclooctanoneHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 67520042HCID 67520042, compound

Conditions

Temperature
100 °C

Procedure

Under the nitrogen gas atmosphere, a solution of cyclooctanone (15.87 mL, 120 mmol) and DMF dimethyl acetal was heated and stirred at 100° C. for 12 hours. After that, the solvent was removed by distillation under reduced pressure and a pale yellow oily matter (16.54 g) was obtained. This was dissolved in methanol (50 mL), and methyl cyanoacetate (8.87 mL, 100.37 mmol) was added and stirred at room temperature. The precipitated solid was separated by filtration and washed with diethyl ether, and the desired compound was obtained as a colorless solid (13.8 g, 49%, and mp: 220-224° C.).

Workup

  1. customAfter that, the solvent was removed by distillation under reduced pressure
  2. customa pale yellow oily matter (16.54 g) was obtained
  3. stirringstirred at room temperature
  4. customThe precipitated solid was separated by filtration
  5. washwashed with diethyl ether

Sources & evidence

ORD record
ord-02ca8d46308348e9bfe25ed8507268f0
Source dataset
uspto-grants-2012_05
Patent number
US08178681B2

Reaction notes

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