Acetic Anhydride → HCID 178499532, compound

HRID 1941781Notes

Reaction equation

C(O/C(=[C:6]1/[C:7]([CH2:18][C:19]([O:21][CH3:22])=[O:20])=[N:8][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10]/1=[O:11])/C)C.C(OC(=O)C)(=O)C.CC(OCC)(OCC)OCC>>[OH:11][C:10]1[N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:8]=[C:7]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH:6]=1

Participants

Reactant 3

HCID 7918Acetic Anhydride

HCID 66221Triethyl orthoacetate

HCID 1512467HCID 1512467, compound

Product 1

HCID 178499532HCID 178499532, compound

Procedure

Methyl [(4Z)-4-(1-ethoxyethylidene)-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl]acetate (Compound of Formula (VII), Scheme 1). 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

additionThe mixture of the

Sources & evidence

ORD record: ord-e1f68c992783411c898992242c361303
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389518B2

Reaction notes

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