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

HRID 717211

反応式

HRID 717211 の反応式
[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

参加物

6

反応物 4

HCID 7859Propargyl alcoholHCID 8471TriethylamineHCID 12143(Z)-Benzaldehyde oximeHCID 31398Chlorosuccinimide2 回

生成物 1

HCID 2763417(3-Phenyl-5-isoxazolyl)methanol収率 76.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-5429e1783feb4fff95493802e03cf19a
出典データセット
uspto-grants-2015_11
特許番号
US09193718B2

関連ノート

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