Benzyl Bromide → HCID 178501330、化合物

HRID 409480ノート

反応式

HRID 409480 の反応式
[CH3:1][O:2][C:3]([CH:5]1[CH2:8][CH:7]([OH:9])[CH2:6]1)=[O:4].[H-].[Na+].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C=O)C>[CH3:1][O:2][C:3]([C@H:5]1[CH2:8][C@H:7]([O:9][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:6]1)=[O:4]

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 12815112Cyclobutanecarboxylic acid, 3-hydroxy-, methyl ester

生成物 1

HCID 178501330HCID 178501330、化合物収率 15.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To a solution of cis-trans mixture of 3-hydroxy-cyclobutanecarboxylic acid methyl ester (1.30 g, 10 mmol) in DMF 13 mL is added NaH (50% in oil, 720 mg, 15 mmol) at 0° C. After stirring at 0° C. for 15 minutes, benzyl bromide (1.43 ml, 12 mmol) is added at 0° C. The mixture is stirred at room temperature for 2 hours and quenched with H2O. The solution is extracted with EtOAc. The organic layer is washed with H2O and brine, dried over MgSO4 and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent; hexane/EtOAc) to give trans-3-benzyloxy-cyclobutanecarboxylic acid methyl ester (340 mg, 15.4%). TLC (hexane/EtOAc, 5:1) Rf 0.40.

後処理

  1. stirringThe mixture is stirred at room temperature for 2 hours
  2. customquenched with H2O
  3. extractionThe solution is extracted with EtOAc
  4. washThe organic layer is washed with H2O and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by silica gel column chromatography (eluent; hexane/EtOAc)

出典と根拠

ORDレコード
ord-81c8eed42ce64beea60a9559eae6bfbd
出典データセット
uspto-grants-2014_06
特許番号
US08759365B2

反応ノート

読み込み中…