Acetic Acid → HCID 70850764, compound

HRID 1526499Notes

Reaction equation

HRID 1526499 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH2:5][CH:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:3]1.[C:13]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])#[N:14].CC(O)=O>C1(C)C=CC=CC=1>[C:13]([C:15](=[C:2]1[CH2:7][CH2:6][CH2:5][CH:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:3]1)[C:16]([O:18][CH2:19][CH3:20])=[O:17])#[N:14]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7764Ethyl cyanoacetateHCID 118096Ethyl 3-oxocyclohexanecarboxylate

Product 1

HCID 70850764HCID 70850764, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into a 500-mL round-bottom flask, was placed ethyl 3-oxocyclohexane-1-carboxylate (7 g, 41.13 mmol, 1.00 equiv), ethyl 2-cyanoacetate (6.5 g, 57.46 mmol, 1.40 equiv), AcOH (0.8 mL) and NH4OAc (300 mg) in toluene (150 mL). The resulting solution was heated to reflux overnight in presence of a Dean-Stark. After the starting 4 was consumed completely, the resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:9) to give the corresponding ethyl 3-(1-cyano-2-ethoxy-2-oxoethylidene)cyclohexane-1-carboxylate (8.0 g, 73%) as yellow oil.

Workup

  1. customInto a 500-mL round-bottom flask, was placed
  2. temperatureThe resulting solution was heated
  3. temperatureto reflux overnight in presence of a Dean-Stark
  4. customAfter the starting 4 was consumed completely
  5. concentrationthe resulting mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-038ea3b347634acf9eb8742e70457ff9
Source dataset
uspto-grants-2015_07
Patent number
US09085586B2

Reaction notes

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