Acetic Acid → 2-Cyanoethyl 2-(4-cyano-2-methoxybenzylidene)-3-oxobutanoate

HRID 2170961Notes

Reaction equation

HRID 2170961 reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[O:11][CH3:12])=O.[O:13]=[C:14]([CH3:23])[CH2:15][C:16]([O:18][CH2:19][CH2:20][C:21]#[N:22])=[O:17].C(O)(=O)C.N1CCCCC1>ClCCl>[C:7]([C:6]1[CH:9]=[CH:10][C:3]([CH:1]=[C:15]([C:14](=[O:13])[CH3:23])[C:16]([O:18][CH2:19][CH2:20][C:21]#[N:22])=[O:17])=[C:4]([O:11][CH3:12])[CH:5]=1)#[N:8]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 123604062-Cyanoethyl 3-oxobutanoateHCID 166592514-Formyl-3-methoxybenzonitrile

Product 1

HCID 685996632-Cyanoethyl 2-(4-cyano-2-methoxybenzylidene)-3-oxobutanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.00 g (18.62 mmol) of the compound from Example 10A, 3.18 g (20.48 mmol) of 2-cyanoethyl 3-oxobutanoate [Yamamoto, T., et al., Bioorg. Med. Chem. Lett. 16, 798-802 (2006)], 213 μl (3.72 mmol) of acetic acid and 368 μl (3.72 mmol) of piperidine are dissolved in 50 ml of anhydrous dichloromethane and stirred under reflux with a water trap overnight. The volatile components are then removed in a rotary evaporator, and the residue is purified by column chromatography (silica gel; mobile phase: gradient cyclohexane/ethyl acetate 7:3→1:1). 2.77 g (48% of theory) of the title compound are obtained as a mixture of the E/Z isomers.

Workup

  1. temperatureunder reflux with a water trap overnight
  2. customThe volatile components are then removed in a rotary evaporator
  3. customthe residue is purified by column chromatography (silica gel; mobile phase: gradient cyclohexane/ethyl acetate 7:3→1:1)

Sources & evidence

ORD record
ord-2f03198acea647c990eec5e5a51e76e9
Source dataset
uspto-grants-2015_06
Patent number
US09051316B2

Reaction notes

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