Acetic Anhydride → HCID 1512467, compound

HRID 1520726Notes

Reaction equation

HRID 1520726 reaction equation
[OH:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[C:4]([CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH:3]=1.[C:18]([O:21][C:22](=O)[CH3:23])(=O)[CH3:19].CC(OCC)(OCC)OCC>>[CH3:17][O:16][C:14](=[O:15])[CH2:13][C:4]1=[N:5][N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:2](=[O:1])/[C:3]/1=[C:18](\[O:21][CH2:22][CH3:23])/[CH3:19]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 66221Triethyl orthoacetateHCID 178499532HCID 178499532, compound

Product 1

HCID 1512467HCID 1512467, compoundYield 80%

Procedure

The mixture of the above obtained methyl (5-hydroxy-1-phenyl-1H-pyrazol-3-yl)acetate (Compound of Formula (IV), 1.85 g), acetic anhydride (1.00 ml) and MeC(OEt)3 (2.50 ml) was refluxed for 1 h. and left overnight at an ambient temperature. Resulting precipitate was collected by filtration and washed with ethyl ether (10 ml) in order to obtain crude product methyl[(4Z)-4-(1-ethoxyethylidene)-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl]acetate (1.20 g, 80% purity) in 50% yields. 1HNMR (400 MHz, CDCl3, ppm): 1.42 (3H, t, 7.1 Hz), 2.78 (3H, s), 3.73 (3H, s), 3.76 (2H, s), 4.31 (2H, q, 6.9 Hz), 7.16 (1H, t, 7.2 Hz), 7.37 (2H, t, 7.6 Hz), 7.97 (2H, d, 8.0 Hz). MS (ESI+): 303.3; MS (ESI−): 301.2.

Workup

  1. additionThe mixture of the
  2. temperaturewas refluxed for 1 h.
  3. customResulting precipitate
  4. filtrationwas collected by filtration
  5. washwashed with ethyl ether (10 ml) in order

Sources & evidence

ORD record
ord-18d249a3ab3448f48a0ba9a2a0498a31
Source dataset
uspto-grants-2015_07
Patent number
US09073919B2

Reaction notes

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