Acetic Acid → HCID 131733023, compound

HRID 1776713Notes

Reaction equation

HRID 1776713 reaction equation
[CH3:1][C:2]1([CH3:8])[CH2:6][CH2:5][C:4](=O)[CH2:3]1.[C:9]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])#[N:10].[Cl-].[NH4+].C(O)(=O)C>C1(C)C=CC=CC=1>[C:9](/[C:11](=[C:4]1\[CH2:3][C:2]([CH3:8])([CH3:1])[CH2:6][CH2:5]\1)/[C:12]([O:14][CH2:15][CH3:16])=[O:13])#[N:10]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7764Ethyl cyanoacetateHCID 25517Ammonium ChlorideHCID 6431023,3-Dimethylcyclopentan-1-one

Product 1

HCID 131733023HCID 131733023, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a round bottomed flask equipped with a stir bar, reflux condenser, and Dean Stark trap were added 3,3-dimethylcyclopentanone (3.4 g, 30 mmol), toluene (50 mL), and ethyl 2-cyanoacetate (3.4 g, 30 mmol), ammonium chloride (231 mg, 3 mmol) and acetic acid (0.36 mL, 6 mmol). The reaction mixture was refluxed for 24 h. The reaction was cooled to RT and concentrated to dryness. The residue was diluted with water (100 mL) and extracted with ethyl acetate (2×100 mL). The combined organic phases were dried with Na2SO4, concentrated to dryness subjected to FCC to afford the title compound as colorless oil.

Workup

  1. customTo a round bottomed flask equipped with a stir bar
  2. temperaturereflux condenser
  3. temperatureThe reaction mixture was refluxed for 24 h
  4. concentrationconcentrated to dryness
  5. additionThe residue was diluted with water (100 mL)
  6. extractionextracted with ethyl acetate (2×100 mL)
  7. dry with materialThe combined organic phases were dried with Na2SO4
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-341b1e11879b4f2688d1732753dd3aec
Source dataset
uspto-grants-2016_02
Patent number
US09265770B2

Reaction notes

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