Borane → Ethyl 5-(hydroxymethyl)-4'-methylbiphenyl-3-carboxylate

HRID 1845256ノート

反応式

HRID 1845256 の反応式
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]([C:19](O)=[O:20])[CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[CH:11]=1)=[O:5])[CH3:2].B>O1CCCC1>[OH:20][CH2:19][C:8]1[CH:7]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:11]=[C:10]([C:12]2[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=2)[CH:9]=1

参加物

4

反応物 2

HCID 6331BoraneHCID 581879575-(Ethoxycarbonyl)-4'-methylbiphenyl-3-carboxylic acid

生成物 1

HCID 58188190Ethyl 5-(hydroxymethyl)-4'-methylbiphenyl-3-carboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

To a stirred solution of 5-(ethoxycarbonyl)-4′-methylbiphenyl-3-carboxylic acid (2.66 g, 8.89 mmol) in dry tetrahydrofuran (40 mL) at 0° C. under an atmosphere of nitrogen was added 1 M of borane solution in tetrahydrofuran (20 mL, 20 mmol). The reaction was stirred at 0° C. for 30 minutes after the addition was complete, and then the cooling bath was removed. After being stirred for 2 hours at room temperature, the reaction mixture was cooled at 0° C. and quenched by addition of 2 M aq. HCl (30 mL). The mixture was stirred for 1 hour at room temperature, and then extracted with EtOAc (50 mL×3). The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered, and concentrated. The residue was purified by silica gel column to afford the title compound.

後処理

  1. additionafter the addition
  2. customthe cooling bath was removed
  3. stirringAfter being stirred for 2 hours at room temperature
  4. temperaturethe reaction mixture was cooled at 0° C.
  5. customquenched by addition of 2 M aq. HCl (30 mL)
  6. stirringThe mixture was stirred for 1 hour at room temperature
  7. extractionextracted with EtOAc (50 mL×3)
  8. washThe combined organic layers were washed with brine
  9. dry with materialdried over anhydrous MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue was purified by silica gel column

出典と根拠

ORDレコード
ord-423d5fa623ce4df7b5720b5c278a8f8c
出典データセット
uspto-grants-2015_02
特許番号
US08946439B2

反応ノート

読み込み中…