3-(4-Fluorophenyl)-2-propenoic acid → 1-[1-(4-Cyanophenyl)-4-(4-fluorophenyl)-2-oxobutyl]-1,2,4-triazole

HRID 1737871Notes

Reaction equation

HRID 1737871 reaction equation
[C:1]([C:3]1[CH:14]=[CH:13][C:6]([CH2:7][N:8]2[CH:12]=[N:11][CH:10]=[N:9]2)=[CH:5][CH:4]=1)#[N:2].[Li]CCCC.[F:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][C:29](OCC)=[O:30])=[CH:23][CH:22]=1.FC1C=CC(C=CC(O)=O)=CC=1>>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:7]([N:8]2[CH:12]=[N:11][CH:10]=[N:9]2)[C:29](=[O:30])[CH2:28][CH2:27][C:24]2[CH:25]=[CH:26][C:21]([F:20])=[CH:22][CH:23]=2)=[CH:13][CH:14]=1)#[N:2]

Participants

5

Reactant 4

HCID 980703-(4-Fluorophenyl)-2-propenoic acidHCID 75376164-(1,2,4-Triazol-1-ylmethyl)benzonitrileHCID 11816416Benzenepropanoic acid, 4-fluoro-, ethyl esterHCID 178418339Butyllithium

Product 1

HCID 218435801-[1-(4-Cyanophenyl)-4-(4-fluorophenyl)-2-oxobutyl]-1,2,4-triazole

Procedure

1-[1-(4-cyanophenyl)-4-(4-fluorophenyl)-2-oxobutyl]-1,2,4-triazole is prepared according to the procedure described in Example 1 starting from 1-(4-cyanobenzyl)-1,2,4-triazole (1.7 g, 0.0092 mol), n-BuLi (0.0108 mol) and ethyl 3-(4-fluorophenyl)propionate (2.3 g, 0.0117 mol) prepared from 4-fluorocinnamic acid by esterification and hydrogenation. The product is purified by flash chromatography methylene chloride-methanol (95:5) as eluent.

Workup

  1. customThe product is purified by flash chromatography methylene chloride-methanol (95:5) as eluent

Sources & evidence

ORD record
ord-5bdc9d226d0f4139b19173e36e35b09e
Source dataset
uspto-grants-1999_10
Patent number
US05962495

Reaction notes

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