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

HRID 58623

반응식

HRID 58623 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ef0452aa01e04e21813141893bd989e4
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434722B2

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