Ammonia → HCID 86674767, compound

HRID 927572Notes

Reaction equation

HRID 927572 reaction equation
[CH3:1][C:2]1([CH3:9])[CH2:7][CH2:6][CH2:5][C:4](=O)[CH2:3]1.[C:10]([O:14]C)(=O)[C:11]#[CH:12].[NH3:16]>>[CH3:1][C:2]1([CH3:9])[CH2:3][C:4]2[NH:16][C:10](=[O:14])[CH:11]=[CH:12][C:5]=2[CH2:6][CH2:7]1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 13536Methyl propiolateHCID 76322Cyclohexanone, 3,3-dimethyl-

Product 1

HCID 86674767HCID 86674767, compoundYield 55.4%

Conditions

Temperature
140 °C

Procedure

A solution of 3,3-dimethylcyclohexanone (10 g, 71.3 mmol) and methyl propiolate (11.5 g, 136 mmol) in ammonia (390 ml, 2.73 mol) was heated and stirred in an autoclave at 140° C. for 16 h. The autoclave was cooled to ambient temperature, and the reaction mixture was transferred into a 1 L round-bottomed flask and was evaporated in vacuo to give a solid residue which was purified by gradient chromatography on silica with ethyl acetate in heptane to give 7.0 g (55%) of the title compound as colorless oil; LC-MS (UV peak area/EIC) 85%, 178.1228 (M+H)+.

Workup

  1. temperatureThe autoclave was cooled to ambient temperature
  2. customthe reaction mixture was transferred into a 1 L round-bottomed flask
  3. customwas evaporated in vacuo
  4. customto give a solid residue which
  5. customwas purified by gradient chromatography on silica with ethyl acetate in heptane

Sources & evidence

ORD record
ord-cc1169dae2b4457f8547daee749d165a
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Reaction notes

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