Diethyl Ether → HCID 178454586, compound

HRID 862103Notes

Reaction equation

HRID 862103 reaction equation
[C:1]([O:5]/[N:6]=[CH:7]\[C:8]1[C:9]([C:14](=[O:23])[C:15]2[CH:20]=[C:19]([Br:21])[CH:18]=[CH:17][C:16]=2[OH:22])=[N:10][CH:11]=[CH:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].CC(C)=[O:26].OS(O)(=O)=O.O=[Cr](=O)=O.C(OCC)C>CC(C)=O>[C:1]([O:5]/[N:6]=[C:7](\[OH:26])/[C:8]1[CH:13]=[CH:12][CH:11]=[N:10][C:9]=1[C:14](=[O:23])[C:15]1[CH:20]=[C:19]([Br:21])[CH:18]=[CH:17][C:16]=1[OH:22])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 88351575HCID 88351575, compoundHCID 131709961Jones' reagent

Product 1

HCID 178454586HCID 178454586, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of (Z)-2-(5-bromo-2-hydroxybenzoyl)-3-formylpyridine O-t-butyloxime (500 mg) in acetone (4 ml) was added, at room temperature, Jones reagent (1 ml), and the mixture was stirred for 30 minutes. To the reaction mixture was added diethyl ether. Insolubles then formed were filtered off. To the filtrate was added a small volume of isopropyl alcohol, and the mixture was concentrated. The concentrate was purified by means of a silica gel column chromatography (eluent: diethyl ether) to give (Z)-2-(5-bromo-2-hydroxybenzoyl)nicotinic acid O-t-butyloxime (240 mg (Compound 138).

Workup

  1. customInsolubles then formed
  2. filtrationwere filtered off
  3. additionTo the filtrate was added a small volume of isopropyl alcohol
  4. concentrationthe mixture was concentrated
  5. customThe concentrate was purified by means of a silica gel column chromatography (eluent: diethyl ether)

Sources & evidence

ORD record
ord-c7db33ec6244490a9a3125db0e0e46ed
Source dataset
uspto-grants-1998_02
Patent number
US05716971

Reaction notes

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