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

HRID 2113907노트

반응식

HRID 2113907 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

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

후처리

  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)

출처 및 근거

ORD 기록
ord-6021b36f6361478ba2cfafada77afcf8
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07432293B2

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