Water → Diflunisal Isopropyl Ester

HRID 1259020

反応式

HRID 1259020 の反応式
C1N=CN(C(N2C=NC=C2)=O)C=1.[CH:13]1[C:18]([C:19]2[CH:20]=[CH:21][C:22]([F:26])=[CH:23][C:24]=2[F:25])=[CH:17][C:16]([C:27]([OH:29])=[O:28])=[C:15]([OH:30])[CH:14]=1.[CH:31](O)([CH3:33])[CH3:32].O>CN(C=O)C>[F:25][C:24]1[CH:23]=[C:22]([F:26])[CH:21]=[CH:20][C:19]=1[C:18]1[CH:13]=[CH:14][C:15]([OH:30])=[C:16]([C:27]([O:29][CH:31]([CH3:33])[CH3:32])=[O:28])[CH:17]=1

参加物

6

反応物 4

HCID 962WaterHCID 3059DiflunisalHCID 3776IsopropanolHCID 682631,1'-Carbonyldiimidazole

生成物 1

HCID 67954033Diflunisal Isopropyl Ester収率 41.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

CDI (972 mg, 5.99 mmol) was added to a solution of diflunisal (1.50 g, 5.99 mmol) in DMF (30 mL). The reaction mixture was stirred at 50° C. for 2 h and isopropyl alcohol (1.15 mL, 14.97 mmol) was dropwise added. The reaction mixture was stirred at 50° C. for 3 h and allowed to reach r.t. It was poured into H2O (50 mL) and extracted with Et2O (2×60 mL). The organic layer was washed with NaHCO3 (20 mL, saturated aqueous solution), dried over Na2SO4 (anhydrous), filtered and concentrated. The crude residue was flash chromatographed on SiO2 (15% EtOAc/hexanes) to furnish 720 mg of isopropyl 2′,4′-difluoro-4-hydroxybiphenyl-3-carboxylate (white solid, yield: 41%).

後処理

  1. stirringThe reaction mixture was stirred at 50° C. for 3 h
  2. customto reach r.t
  3. extractionextracted with Et2O (2×60 mL)
  4. washThe organic layer was washed with NaHCO3 (20 mL, saturated aqueous solution)
  5. dry with materialdried over Na2SO4 (anhydrous)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed on SiO2 (15% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-c17d6866c8e84c39bde6c2e55fd40b9c
出典データセット
uspto-grants-2013_06
特許番号
US08466197B2

関連ノート

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