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

HRID 1593615노트

반응식

HRID 1593615 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

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)−.

후처리

  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

출처 및 근거

ORD 기록
ord-5fe8248b5ef84d848efa74c3fdf50697
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07297704B2

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