Oxalyl chloride → (Z)-5-Fluoro-2-methyl-1-(3,4,5-trimethoxybenzylidene)-3-indenylacetyl chloride

HRID 2186567Notes

Reaction equation

HRID 2186567 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)/[C:7](=[CH:11]\[C:12]1[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=1)/[C:6]([CH3:24])=[C:5]2[CH2:25][C:26]([OH:28])=O.C(Cl)(=O)C([Cl:32])=O>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)/[C:7](=[CH:11]\[C:12]1[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=1)/[C:6]([CH3:24])=[C:5]2[CH2:25][C:26]([Cl:32])=[O:28]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 9864863(Z)-5-fluoro-2-methyl-1-(3,4,5-trimethoxybenzylidene)-3-indenylacetic acid

Product 1

HCID 86755162(Z)-5-Fluoro-2-methyl-1-(3,4,5-trimethoxybenzylidene)-3-indenylacetyl chloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(Z)-5-fluoro-2-methyl-1-(3,4,5-trimethoxybenzylidene)-3-indenylaceticacid (20.64g, 54.70mmol) in THF (150 ml) is allowed to react with oxalylchloride (2 M in CH2Cl2; 35 ml; 70 mmol) under reflux conditions (24 h). The solvent is evaporated to yield the title compound, which is used as such in the next step.

Workup

  1. customThe solvent is evaporated

Sources & evidence

ORD record
ord-f05538304a5d4e7dbfe6ffd35743de16
Source dataset
uspto-grants-2002_06
Patent number
US06403831B1

Reaction notes

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