Water → 5-Isoxazolecarboxylic acid, 4,5-dihydro-3-phenyl-, methyl ester

HRID 1918530Notes

Reaction equation

HRID 1918530 reaction equation
[OH:1][N:2]=[C:3](Cl)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:11]([O:15][CH3:16])(=[O:14])[CH:12]=[CH2:13].C(=O)(O)[O-].[Na+].O>C(OCC)(=O)C>[C:4]1([C:3]2[CH2:13][CH:12]([C:11]([O:15][CH3:16])=[O:14])[O:1][N:2]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7294Methyl AcrylateHCID 516892Sodium BicarbonateHCID 2756315N-hydroxybenzenecarboximidoyl chloride

Product 1

HCID 107746025-Isoxazolecarboxylic acid, 4,5-dihydro-3-phenyl-, methyl esterYield 73.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of N-hydroxybenzimidoyl chloride (0.500 g; 3.21 mmol) in ethyl acetate (4 mL) was added dropwise to the mixture of methyl acrylate (0.58 mL; 6.43 mmol), sodium bicarbonate (0.818 g; 9.64 mmol), water 0.1 mL and ethyl acetate (16 mL) at room temperature and the resulting mixture was stirred for 22 hours. The solid was eliminated by filtration and washed with ethyl acetate. The filtrate was evaporated and the residue purified by flash chromatography on silica gel (eluent: 15 to 100% dichloromethane in heptane) to afford 0.482 g (73%) of methyl 3-phenyl-4,5-dihydroisoxazole-5-carboxylate as a white solid.

Workup

  1. filtrationThe solid was eliminated by filtration
  2. washwashed with ethyl acetate
  3. customThe filtrate was evaporated
  4. customthe residue purified by flash chromatography on silica gel (eluent: 15 to 100% dichloromethane in heptane)

Sources & evidence

ORD record
ord-1c45ced809fd4a07afb1ccdf32f2f1b0
Source dataset
uspto-grants-2013_12
Patent number
US08618138B2

Reaction notes

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