Pyridine → Methyl 3-(5-p-tolylisoxazol-3-yl)benzoate

HRID 2113907Notes

Reaction equation

HRID 2113907 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10](Cl)=[N:11][OH:12])[CH:5]=1.[C:15]([C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1)#[CH:16].N1C=CC=CC=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[CH:16]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)[O:12][N:11]=2)[CH:5]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 13018p-EthynyltolueneHCID 85867392Methyl 3-[chloro(hydroxyimino)methyl]benzoate

Product 1

HCID 57907091Methyl 3-(5-p-tolylisoxazol-3-yl)benzoate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In a 25 ml round flask, 1.9 g (8.9 mmol) of 3-[chloro-(hydroxyimino)-methyl]-benzoic acid methyl ester and 1.03 g (8.9 mmol) of 1-ethynyl-4-methyl-benzene are dissolved in 12 ml of CHCl3 at 0° C. To this solution, 36 μl (0.4 mmol, 0.05 eq.) of pyridine and subsequently 1.24 ml (8.9 mmol) of triethyl amine are added and the mixture is stirred under warming to room temperature for 2 h. Then, the mixture is poured onto water, extracted twice with CH2Cl2, the organic layers are dried with brine and Na2SO4 and then concentrated. Chromatographic purification (250 g SiO2; gradient elution, eluent: hexane/ethyl acetate 95:5→9:1) yields the title compound as a white solid. Mass spectrum: m/z (M+H)+: 294.2

Workup

  1. additionThen, the mixture is poured onto water
  2. extractionextracted twice with CH2Cl2
  3. dry with materialthe organic layers are dried with brine and Na2SO4
  4. concentrationconcentrated
  5. customChromatographic purification (250 g SiO2; gradient elution, eluent: hexane/ethyl acetate 95:5→9:1)

Sources & evidence

ORD record
ord-6021b36f6361478ba2cfafada77afcf8
Source dataset
uspto-grants-2008_10
Patent number
US07432293B2

Reaction notes

Loading…