Pyridine → (3-Phenyl-5-isoxazolyl)methanol

HRID 868923

반응식

HRID 868923 반응식
[CH:1](=[N:8]/[OH:9])/[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClN1[C:15](=[O:16])[CH2:14][CH2:13]C1=O.N1C=CC=CC=1.C(O)C#C.CCN(CC)CC>C1COCC1>[C:2]1([C:1]2[CH:13]=[C:14]([CH2:15][OH:16])[O:9][N:8]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 5

HCID 1049PyridineHCID 7859Propargyl alcoholHCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 5324470Syn-benzaldehyde oxime

생성물 1

HCID 2763417(3-Phenyl-5-isoxazolyl)methanol수율 36.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

(Z)-Benzaldehyde oxime (3.4 g, 28.2 mmol) was dissolved in anhydrous THF (50 mL) and cooled to 0° C. N-Chlorosuccinimide (5.63 g, 42.3 mmol) and pyridine (221 mg, 2.8 mmol) were added and the mixture was stirred at room temperature for 1 hour. Prop-2-yn-1-ol (1.89 g, 33.4 mmol) and NEt3 (286 mg, 2.8 mmol) were added and the mixture was heated at reflux for 2 hours. The reaction was cooled and quenched with water, extracted with EtOAc and dried over anhydrous sodium sulfate. The solution was concentrated under vacuum to give a crude product, which was purified by column chromatography to afford (3-phenylisoxazol-5-yl)methanol as a white solid (1.8 g).

후처리

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 2 hours
  3. temperatureThe reaction was cooled
  4. customquenched with water
  5. extractionextracted with EtOAc
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationThe solution was concentrated under vacuum
  8. customto give a crude product, which
  9. customwas purified by column chromatography

출처 및 근거

ORD 기록
ord-fa32c6c8264a4fdcb326fb12add69af1
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969349B2

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