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

HRID 1429863Notes

Reaction equation

HRID 1429863 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH2:4][C:5]1[CH:9]=[C:8]([OH:10])[N:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])[N:6]=1.C(O)(=O)C.[CH3:23][C:24](OCC)(OCC)[O:25][CH2:26][CH3:27]>>[CH3:1][O:2][C:3](=[O:18])[CH2:4][C:5]1=[N:6][N:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])[C:8](=[O:10])/[C:9]/1=[C:24](/[O:25][CH2:26][CH3:27])\[CH3:23]

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 MeC(OEt)3 (2.00 ml) was heated at 60° C. for 1 h 15. 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-c39b2f41d6274e998be89189a08ecbb4
Source dataset
uspto-grants-2015_01
Patent number
US08940760B2

Reaction notes

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