Acetic Acid → HCID 118006223, compound

HRID 926496Notes

Reaction equation

HRID 926496 reaction equation
[O:1]=[C:2]([CH2:8][CH3:9])[CH2:3][C:4]([O:6][CH3:7])=[O:5].[N:10]1([C:15]2[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=2)[CH:14]=[CH:13][CH:12]=[N:11]1.N1CCCCC1.C(O)(=O)C>C1C=CC=CC=1.O>[N:10]1([C:15]2[CH:22]=[CH:21][C:18]([CH:19]=[C:3]([C:2](=[O:1])[CH2:8][CH3:9])[C:4]([O:6][CH3:7])=[O:5])=[CH:17][CH:16]=2)[CH:14]=[CH:13][CH:12]=[N:11]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 121699Methyl 3-oxovalerateHCID 27764774-(1H-Pyrazol-1-yl)benzaldehyde

Product 1

HCID 118006223HCID 118006223, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Conditions

Temperature
23 °C

Procedure

A mixture containing methyl 3-oxopentanoate (2.2 g, 17 mmol), 4-(1H-pyrazol-1-yl)benzaldehyde (2.5 g, 14 mmol), piperidine (0.3 mL, 3.0 mmol), and acetic acid (0.16 mL, 2.8 mmol) in benzene (70 mL) was heated to 90° C. with removal of water (Dean-Stark trap). After 4 hours, the mixture was cooled to 23° C. and then concentrated to provide the title compound. The residue (mixture of alkene isomers) was taken onto the next step without further purification.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-056f960a66064766b255c25f4c94056f
Source dataset
uspto-grants-2016_03
Patent number
US09284308B2

Reaction notes

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