Acetic Acid → HCID 86693764, compound

HRID 1506915Notes

Reaction equation

HRID 1506915 reaction equation
[C:1]([CH2:3][C:4]([O:6][CH3:7])=[O:5])#[N:2].[CH3:8][CH:9]([C:11](=O)[CH2:12][CH2:13][CH3:14])[CH3:10].C([O-])(=O)C.[NH4+].C(O)(=O)C>C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[C:1]([C:3](=[C:11]([CH2:12][CH2:13][CH3:14])[CH:9]([CH3:10])[CH3:8])[C:4]([O:6][CH3:7])=[O:5])#[N:2]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 7747Methyl cyanoacetateHCID 238472-Methyl-3-hexanoneHCID 517165Ammonium Acetate

Product 1

HCID 86693764HCID 86693764, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl cyanoacetate (1.98 g), 2-methylhexan-3-one (3.76 g), ammonium acetate (0.196 g) and glacial acetic acid (0.288 ml) in toluene (10 ml) was stirred and heated at reflux with removal of water using a Dean and Stark apparatus for 6 hours. After cooling to room temperature the mixture was diluted with ethyl acetate and washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica eluting with a mixture of ethyl acetate and pentane (2%) to give methyl 2-cyano-3-propyl-4-methylpent-2-enoate (as a mixture of E and Z isomers) (2.11 g) as a colourless oil.

Workup

  1. temperatureheated
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness
  6. customthe residue was purified by chromatography on silica eluting with a mixture of ethyl acetate and pentane (2%)

Sources & evidence

ORD record
ord-05b6cbaead2547d8804006c78e7c9644
Source dataset
uspto-grants-2015_12
Patent number
US09221787B2

Reaction notes

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