Acetic Acid → HCID 68717167, compound

HRID 1947247Notes

Reaction equation

HRID 1947247 reaction equation
[CH2:1]([O:3][CH:4]([O:13][CH2:14][CH3:15])[C:5](=[O:12])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:2].[CH:16]([C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][C:19]=1[O:26][CH3:27])=O.C(O)(=O)C.N1CCCCC1>ClCCl>[C:22]([C:21]1[CH:24]=[CH:25][C:18]([CH:16]=[C:6]([C:5](=[O:12])[CH:4]([O:3][CH2:1][CH3:2])[O:13][CH2:14][CH3:15])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:19]([O:26][CH3:27])[CH:20]=1)#[N:23]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 11138577Ethyl 4,4-diethoxy-3-oxobutanoateHCID 166592514-Formyl-3-methoxybenzonitrile

Product 1

HCID 68717167HCID 68717167, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

618.2 mg (2.83 mmol) of ethyl 4,4-diethoxy-3-oxobutanoate [Johnson et al., J. Am. Chem. Soc. 41, 812 (1919)], 500.0 mg (2.58 mmol) of 4-formyl-3-methoxybenzonitrile, 232.0 mg (3.86 mmol) of acetic acid and 43.9 mg (0.51 mmol) of piperidine are dissolved in 20 ml of dichloromethane and heated under reflux with an inverse water trap ovemight. Cooling is followed by washing twice with water, and the organic phase is dried with magnesium sulfate. The solvent is removed in a rotary evaporator, and the residue is purified by column chromatography (silica gel, mobile phase:cyclohexane/ethyl acetate 4:1). 824 mg (77.0% of theory) of the title compound are obtained as a mixture of the E/Z isomers.

Workup

  1. temperatureheated
  2. temperatureunder reflux with an inverse water trap ovemight
  3. temperatureCooling
  4. washby washing twice with water
  5. dry with materialthe organic phase is dried with magnesium sulfate
  6. customThe solvent is removed in a rotary evaporator
  7. customthe residue is purified by column chromatography (silica gel, mobile phase:cyclohexane/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-7b6fffb346f54cb396a1cab424fa0554
Source dataset
uspto-grants-2013_03
Patent number
US08399471B2

Reaction notes

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