Ethyl orthoformate → (4Z)-4-[(ethoxy)methylidene]-2,5-bis(2-fluorophenyl)-2,4-dihydro-3H-pyrazol-3-one

HRID 341047Notes

Reaction equation

HRID 341047 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12](=[O:13])[CH2:11][C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[F:20])=[N:9]1.[CH2:21]([O:23][CH:24](OCC)OCC)[CH3:22]>>[CH2:21]([O:23]/[CH:24]=[C:11]1\[C:12](=[O:13])[N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[N:9]=[C:10]\1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[F:20])[CH3:22]

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 671115152,5-bis(2-fluorophenyl)-2,4-dihydro-3H-pyrazol-3-one

Product 1

HCID 68153972(4Z)-4-[(ethoxy)methylidene]-2,5-bis(2-fluorophenyl)-2,4-dihydro-3H-pyrazol-3-one

Procedure

2,5-Bis(2-fluorophenyl)-2,4-dihydro-3H-pyrazol-3-one [(Example 107, Step 1), 85 mg, 0.31 mmol] and triethylorthoformate (0.057 mL, 0.34 mmol, 1.1 equiv) were combined and placed into a preheated oil bath at 100° C. for 1 hour. The mixture was cooled to ambient temperature and concentrated in vacuo, providing the titled compound.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f494f8e4590742d88e49e63b19342904
Source dataset
uspto-grants-2014_11
Patent number
US08895580B2

Reaction notes

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