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

HRID 1918530노트

반응식

HRID 1918530 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-1c45ced809fd4a07afb1ccdf32f2f1b0
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618138B2

반응 노트

불러오는 중…