alpha-Ethynylbenzenemethanol → Ethyl 5-(hydroxy(phenyl)methyl)isoxazole-3-carboxylate

HRID 58623

反応式

HRID 58623 の反応式
[C:1]1([CH:7]([OH:10])[C:8]#[CH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl/[C:12](=[N:18]\[OH:19])/[C:13]([O:15][CH2:16][CH3:17])=[O:14].C(=O)([O-])O.[Na+]>C(OCC)(=O)C.O>[OH:10][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8]1[O:19][N:18]=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:9]=1

参加物

6

反応物 3

HCID 20155alpha-EthynylbenzenemethanolHCID 516892Sodium BicarbonateHCID 95760052-Chloro-2-hydroxyiminoacetic acid ethyl ester

生成物 1

HCID 66831982Ethyl 5-(hydroxy(phenyl)methyl)isoxazole-3-carboxylate収率 70%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

1-phenylprop-2-yn-1-ol (0.802 mL, 6.60 mmol) was added to a mixture of (Z)-ethyl 2-chloro-2-(hydroxyimino)acetate (0.50 g; 3.30 mmol) and sodium hydrogen carbonate (0.554 g; 6.60 mmol) in ethyl acetate (15 mL) and water (0.2 mL) and stirred at room temperature for 24 hours. The resulting mixture was filtered and concentrated under reduced pressure. The crude mixture was purified by flash chromatography on silica (eluent 2 to 40% ethyl acetate in heptane) to yield 0.571 g (70%) of ethyl 5-(hydroxy(phenyl)methyl)isoxazole-3-carboxylate as a colorless oil.

後処理

  1. filtrationThe resulting mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. customThe crude mixture was purified by flash chromatography on silica (eluent 2 to 40% ethyl acetate in heptane)

出典と根拠

ORDレコード
ord-ef0452aa01e04e21813141893bd989e4
出典データセット
uspto-grants-2016_09
特許番号
US09434722B2

関連ノート

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