Potassium Carbonate → HCID 67773395、化合物

HRID 2367922ノート

反応式

HRID 2367922 の反応式
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[C:7]([OH:14])[CH:8]=[CH:9][CH:10]=2)[N:5]=1.[C:16]([O:20][C:21](=[O:28])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]Br)([CH3:19])([CH3:18])[CH3:17].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:16]([O:20][C:21](=[O:28])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][O:14][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[N:5]=[C:4]([C:3]([O:2][CH3:1])=[O:15])[CH:13]=[CH:12]2)([CH3:19])([CH3:18])[CH3:17]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 11550568Tert-butyl 6-bromohexanoateHCID 12336161Methyl 8-Hydroxyquinoline-2-Carboxylate

生成物 1

HCID 67773395HCID 67773395、化合物収率 86%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

To a solution of 8-hydroxyquinaldic acid methyl ester (406 mg, 2 mmol, 1 eq.) and t-butyl-6-bromohexanoate (754 mg, 3 mmol, 1.5 eq.) in DMF (5 mL) was added potassium carbonate (828 mg, 6 mmol, 3 eq.). The mixture was stirred vigorously for 3 h at 60° C., and then concentrated in vacuo. The residue was diluted with ethyl acetate, washed with NaH2PO4 buffer (pH 5, 1M) and brine, dried over Na2SO4 and concentrated in vacuo. Crude product was purified by flash chromatography on silica using ethyl acetate:hexanes gradient to provide 617 mg of 1. Yield 86%. MS m/z 374 (M+H)+

後処理

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with ethyl acetate
  3. washwashed with NaH2PO4 buffer (pH 5, 1M) and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customCrude product was purified by flash chromatography on silica

出典と根拠

ORDレコード
ord-086bd1d8b51b4359ab4b6a944e3bdf90
出典データセット
uspto-grants-2014_04
特許番号
US08703700B2

反応ノート

読み込み中…