Thiophenol → Ethyl 3-oxo-4-(phenylthio)cyclohexanecarboxylate

HRID 1593615ノート

反応式

HRID 1593615 の反応式
Br[CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][C:3]1=[O:13].[C:14]1([SH:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[OH-].[Na+]>CCO>[O:13]=[C:3]1[CH:2]([S:20][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4]1

参加物

5

反応物 3

HCID 7969ThiophenolHCID 14798Sodium HydroxideHCID 12917736Ethyl 4-bromo-3-oxocyclohexanecarboxylate

生成物 1

HCID 58999613Ethyl 3-oxo-4-(phenylthio)cyclohexanecarboxylate収率 61.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

実験手順

To a solution of ethyl 4-bromo-3-oxocyclohexanecarboxylate (3.73 g, 15 mmol) in EtOH (30 mL) at 80° C. was added a solution of benzenethiol (1.65 mL, 15 mmol) and NaOH (0.6 g, 15 mmol) in EtOH (100 mL). The suspension was stirred for 1 hour, then was concentrated in vacuo. The residue was diluted with water and extracted with EtOAc. The organic layer was washed with water then brine, then was dried over MgSO4 and concentrated in vacuo. Purification by chromatography on silica gel afforded 2.56 g (61%) of the title compound as a yellow oil: MS (−) 277 (M−H)−.

後処理

  1. concentrationwas concentrated in vacuo
  2. additionThe residue was diluted with water
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with water
  5. dry with materialbrine, then was dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customPurification by chromatography on silica gel

出典と根拠

ORDレコード
ord-5fe8248b5ef84d848efa74c3fdf50697
出典データセット
uspto-grants-2007_11
特許番号
US07297704B2

反応ノート

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