Acetic Acid → methyl [(4E)-1-(2-chlorophenyl)-4-(1-ethoxyethylidene)-5-oxo-4,5-dihydro-1H-pyrazol-3-yl]acetate

HRID 509609Notes

Reaction equation

HRID 509609 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([OH:13])=[CH:11][C:10]([CH2:14][C:15]([O:17][CH3:18])=[O:16])=[N:9]1.C(O)(=O)C.[CH2:23]([O:25][C:26](OCC)(OCC)[CH3:27])[CH3:24]>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12](=[O:13])/[C:11](=[C:23](/[O:25][CH2:26][CH3:27])\[CH3:24])/[C:10]([CH2:14][C:15]([O:17][CH3:18])=[O:16])=[N:9]1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 66221Triethyl orthoacetateHCID 178499531HCID 178499531, compound

Product 1

HCID 86701218methyl [(4E)-1-(2-chlorophenyl)-4-(1-ethoxyethylidene)-5-oxo-4,5-dihydro-1H-pyrazol-3-yl]acetate

Conditions

Temperature
60 °C

Procedure

The mixture of the above obtained methyl [1-(2-chlorophenyl)-5-hydroxy-1H-pyrazol-3-yl]acetate (Compound of Formula (IV), 1.00 g), glacial acetic acid (21 μl, 0.1 equiv.) and 1,1,1-triethoxyethane (2.00 ml) was heated at 60° C. for 1 h15. The resulting red solution was concentrated in vacuo to afford a red syrup that was washed with cyclohexane and then dried in vacuo. Due to its relative instability, no further purification of methyl [(4E)-1-(2-chlorophenyl)-4-(1-ethoxyethylidene)-5-oxo-4,5-dihydro-1H-pyrazol-3-yl]acetate was conducted (1.26 g, quantitative yield). MS(ESI+): 336.8; MS(ESI−): 334.6.

Workup

  1. additionThe mixture of the
  2. concentrationThe resulting red solution was concentrated in vacuo
  3. customto afford a red syrup that
  4. washwas washed with cyclohexane
  5. customdried in vacuo
  6. customDue to its relative instability, no further purification of methyl [(4E)-1-(2-chlorophenyl)-4-(1-ethoxyethylidene)-5-oxo-4,5-dihydro-1H-pyrazol-3-yl]acetate

Sources & evidence

ORD record
ord-6c4d8cfff2c640e7b491861734cf96b2
Source dataset
uspto-grants-2015_08
Patent number
US09096588B2

Reaction notes

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