Propargyl alcohol → (3-Phenyl-5-isoxazolyl)methanol

HRID 717211

반응식

HRID 717211 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.C(O)C#C.C(N(CC)CC)C>ClCCl>[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

6

반응물 4

HCID 7859Propargyl alcoholHCID 8471TriethylamineHCID 12143(Z)-Benzaldehyde oximeHCID 31398Chlorosuccinimide2회

생성물 1

HCID 2763417(3-Phenyl-5-isoxazolyl)methanol수율 76.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

10.0 mmol of benzaldehyde oxime and 30 mL of dry dichloromethane were placed in a 250 mL single-necked round-bottom flask. 1.60 g (12.0 mmol) of N-chlorosuccinimide (NCS) was added under stirring. After NCS was completely dissolved by slightly heating, 0.56 g (10.0 mmol) of 2-propyn-1-ol was added dropwise, and then 20 mL solution of 10.1 g (10.0 mmol) of triethylamine in dichloromethane. After the addition was complete, the system was refluxed. After the completion of the reaction monitored by TLC, the mother liquor was washed with water, dried over anhydrous sodium sulfate, and separated by column chromatography (Vpetroleum ether:Vethyl acetate=5:1-2:1) to give 3-phenyl-5-hydroxymethyl-isoxazole in 76.8% yield.

후처리

  1. temperatureby slightly heating
  2. additionAfter the addition
  3. temperaturethe system was refluxed
  4. washthe mother liquor was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customseparated by column chromatography (Vpetroleum ether:Vethyl acetate=5:1-2:1)

출처 및 근거

ORD 기록
ord-5429e1783feb4fff95493802e03cf19a
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193718B2

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