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

HRID 1918612Notes

Reaction equation

HRID 1918612 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-b37555085a0f42bbb0838341fda5dbf3
Source dataset
uspto-grants-2013_12
Patent number
US08618138B2

Reaction notes

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