Water → Methyl-4-(4-oxo-4H-chromen-3-ylmethyl)-benzoate

HRID 252762

반응식

HRID 252762 반응식
O.[O:2]=[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[O:6][CH2:5][C:4]1=[CH:13][C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][CH:15]=1>CCO.C(OCC)(=O)C>[CH3:21][O:20][C:18](=[O:19])[C:17]1[CH:22]=[CH:23][C:14]([CH2:13][C:4]2[C:3](=[O:2])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][CH:5]=2)=[CH:15][CH:16]=1

참가 물질

5

반응물 2

HCID 962WaterHCID 4240115Methyl 4-(4-oxo-chroman-3-ylidenemethyl)-benzoate

생성물 1

HCID 22478819Methyl-4-(4-oxo-4H-chromen-3-ylmethyl)-benzoate수율 59%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8857Ethyl Acetate용매

반응 조건

온도
70 °C

실험 절차

Water (0.2 ml) and RhCl3.H2O (7 mg, 0.034 mmol) was added to a suspension of compound 260 (200 mg, 0.680 mmol) in EtOH (2 ml) and CHCL3 (2 ml). The reaction mixture was stirred 16 h at 70° C. The reaction mixture was cooled down and diluted in ethyl acetate, washed with brine, dried over anhydrous MgSO4, filtered and concentrated. The crude residue was then purified by flash chromatography on silica gel (0.5-1% MeOH/CH2Cl2) to afford the title compound 261 (118 mg, 59%) as a white solid. 1H NMR: (DMSO) δ (ppm): 8.45 (s, 1H), 8.03 (dd, J=7.9, 1.8 Hz, 1H), 7.87 (d, J=8.4 Hz, 2H), 7.83-7.77 (m, 1H), 7.65 (d, J=8.3 Hz, 1H), 7.50-7.43 (m3, 1H), 3.82 (s, 3H), 3.80 (s, 2H).

후처리

  1. temperatureThe reaction mixture was cooled down
  2. washwashed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was then purified by flash chromatography on silica gel (0.5-1% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-aeb97a9251dc4eb18c81434c77d85f8d
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07868204B2

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