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

HRID 1918530ノート

反応式

HRID 1918530 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-1c45ced809fd4a07afb1ccdf32f2f1b0
出典データセット
uspto-grants-2013_12
特許番号
US08618138B2

反応ノート

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