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

HRID 58543ノート

反応式

HRID 58543 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-49c9bf74fd0d48dda941b59c403ba153
出典データセット
uspto-grants-2016_09
特許番号
US09434722B2

反応ノート

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