4-Chloro-3-(4-chloro-3-formylphenyl)-5-difluoromethoxy-1-methyl-1H-pyrazole → 4-Chloro-3-[4-chloro-3-(4,4-diethoxy-3-oxobut-1-en1-yl)phenyl]-5-difluoromethoxy-1-methyl-1H-pyrazole

HRID 583038Notes

Reaction equation

[CH2:1]([O:3][CH:4]([O:27][CH2:28][CH3:29])[C:5](=[O:26])[CH:6]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH3:2].[Cl:30][C:31]1[C:32]([C:41]2[CH:46]=[CH:45][C:44]([Cl:47])=[C:43]([CH:48]=O)[CH:42]=2)=[N:33][N:34]([CH3:40])[C:35]=1[O:36][CH:37]([F:39])[F:38]>CN(C)C=O>[Cl:30][C:31]1[C:32]([C:41]2[CH:46]=[CH:45][C:44]([Cl:47])=[C:43]([CH:48]=[CH:6][C:5](=[O:26])[CH:4]([O:27][CH2:28][CH3:29])[O:3][CH2:1][CH3:2])[CH:42]=2)=[N:33][N:34]([CH3:40])[C:35]=1[O:36][CH:37]([F:38])[F:39]

Participants

Conditions

Temperature: 85 °C

Procedure

5.1 g of (3,3-diethoxy-2-oxopropylidene)(triphenyl)phosphorane were added to a solution of 2 g (6.2 mmol) of 4-chloro-3-(4-chloro-3-formylphenyl)-5-difluoromethoxy-1-methyl-1H-pyrazole in 20 ml of dimethylformamide, and the mixture was hen heated at 80-90° C. for 5 hours. The mixture was then concentrated and the crude product thus obtained was purified by chromatography on silica gel (eluent: hexane/ethyl acetate=4:1). Yield: 2.1 g.

Workup

concentrationThe mixture was then concentrated

Sources & evidence

ORD record: ord-85dbe288c460481fa905d4b467448c6f
Source dataset: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05928999

Reaction notes

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