Benzyl Bromide → HCID 178501330、化合物

HRID 409482ノート

反応式

HRID 409482 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 34.1%

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 50% NaH (720 mg, 15 mmol) at 0° C. After stirring at 0° C. for 15 min, 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 to give trans-3-benzyloxy-cyclobutanecarboxylic acid methyl ester (750 mg, 34.1%); TLC (hexane/EtOAc, 5:1) Rf 0.35.

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

出典と根拠

ORDレコード
ord-bb0e54cd38844061b868a46be9bd3bdb
出典データセット
uspto-grants-2014_06
特許番号
US08759365B2

反応ノート

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