Acetone → 8-(Benzyloxy)-5-[(2S)oxiranylmethoxy]-3,4-dihydro-2(1H)-quinolinone

HRID 1281481ノート

反応式

HRID 1281481 の反応式
[OH:1][C:2]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6](=[O:13])[NH:7]2.C(=O)([O-])[O-].[K+].[K+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[CH3:28][C:29]([CH3:31])=[O:30]>>[CH2:20]([O:12][C:9]1[CH:10]=[CH:11][C:2]([O:1][CH2:28][C@@H:29]2[CH2:31][O:30]2)=[C:3]2[C:8]=1[NH:7][C:6](=[O:13])[CH2:5][CH2:4]2)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

参加物

5

反応物 4

HCID 180AcetoneHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 1515652(1H)-Quinolinone, 3,4-dihydro-5,8-dihydroxy-

生成物 1

HCID 233813448-(Benzyloxy)-5-[(2S)oxiranylmethoxy]-3,4-dihydro-2(1H)-quinolinone

実験手順

5,8-Dihydroxy-3,4-dihydro-2(1H)-quinolinone (2.0 g, 11.16 mmol) and potassium carbonate (1.8 g, 13.02 mmol) were stirred at reflux in acetone (35 mL). Benzyl bromide (1.33 mL, 11.2 mmol) was added and refluxing continued for 4 hours. The solvents were removed and the reaction mixture partitioned between chloroform and water. The organic phase was washed with brine and dried over anhydrous magnesium sulfate. The solution was filtered and the solvent evaporated to dryness in vacuo. The residue was purified by flash chromatography on silica gel Merck-60 (eluant: 1:1 hexane-ethyl acetate) to yield the title compound (0.80 g, 2.97 mmol).

後処理

  1. temperaturerefluxing
  2. customThe solvents were removed
  3. customthe reaction mixture partitioned between chloroform and water
  4. washThe organic phase was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThe solution was filtered
  7. customthe solvent evaporated to dryness in vacuo
  8. customThe residue was purified by flash chromatography on silica gel Merck-60 (eluant: 1:1 hexane-ethyl acetate)

出典と根拠

ORDレコード
ord-cd5a3f65fdb34c778448468b6b1fecdd
出典データセット
uspto-grants-2002_09
特許番号
US06451814B1

反応ノート

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