Acetic Acid → HCID 69734031, compound

HRID 489403Notes

Reaction equation

HRID 489403 reaction equation
[O:1]=[C:2]([CH2:9][CH2:10][CH3:11])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:12]1([CH:22]=O)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1.N1CCCCC1.C(O)(=O)C>C1C=CC=CC=1>[C:12]1([CH:22]=[C:3]([C:2](=[O:1])[CH2:9][CH2:10][CH3:11])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 61951-NaphthaldehydeHCID 8082PiperidineHCID 238498Ethyl 3-oxohexanoate

Product 1

HCID 69734031HCID 69734031, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of ethyl 3-ketohexanoate (6.6 g), 1-naphthaldehyde (7.34 g), piperidine (1.2 g) and acetic acid (2.25 g) in benzene (50 mL) was heated under reflux for 3 hours and the reaction mixture was dehydrated using a Dean-Stark condenser. The solvent was evaporated and the residue was purified by silica gel column chromatography using an eluent (hexane-ethyl acetate (3:1)) to give ethyl 2-(naphthalen-1-yl)methylene-3-oxohexanoate ((E)/(Z)=1:1 mixture) as a yellow oil. The title compound was obtained as a colorless amorphous solid from ethyl 2-(naphthalen-1-yl)methylene-3-oxohexanoate ((E)/(Z)=1:1 mixture), 3-amino-2-methylpyrazole and p-toluenesulfonic acid.

Workup

  1. temperatureunder reflux for 3 hours
  2. customThe solvent was evaporated
  3. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-53f49cbbcdf543ef811e5bd0a451ead1
Source dataset
uspto-grants-2005_12
Patent number
US06977262B2

Reaction notes

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