Potassium Hydroxide → Ethyl 4-[(4-fluorophenyl)thio]-3-oxocyclohexanecarboxylate

HRID 1593614노트

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HRID 1593614 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].[F:14][C:15]1[CH:20]=[CH:19][C:18]([SH:21])=[CH:17][CH:16]=1.[OH-].[K+]>CCO>[F:14][C:15]1[CH:20]=[CH:19][C:18]([S:21][CH:2]2[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][C:3]2=[O:13])=[CH:17][CH:16]=1

참가 물질

5

반응물 3

HCID 14797Potassium HydroxideHCID 677894-FluorothiophenolHCID 12917736Ethyl 4-bromo-3-oxocyclohexanecarboxylate

생성물 1

HCID 69232235Ethyl 4-[(4-fluorophenyl)thio]-3-oxocyclohexanecarboxylate수율 51%

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

To a solution of ethyl 4-bromo-3-oxocyclohexanecarboxylate (5.2 g, 20.9 mmol) in EtOH (120 mL) at 80° C. was added a solution of 4-fluorobenzenethiol (2.22 mL, 20.9 mmol) and KOH (1.29 g, 22.9 mmol) in EtOH (50 mL). The suspension was stirred for 30 min then filtered. The filtrate was concentrated in vacuo then diluted with water and extracted with diethyl ether. The organic layer was washed with water then brine, then was dried over MgSO4 and concentrated in vacuo. Purification by chromatography on silica gel (15% EtOAc in hexane) afforded the title compound (3.08 g, 51%) as a white solid: mp 96-97° C.; MS (+) 297 (M+H)+.

후처리

  1. filtrationthen filtered
  2. concentrationThe filtrate was concentrated in vacuo
  3. additionthen diluted with water
  4. extractionextracted with diethyl ether
  5. washThe organic layer was washed with water
  6. dry with materialbrine, then was dried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customPurification by chromatography on silica gel (15% EtOAc in hexane)

출처 및 근거

ORD 기록
ord-cb0ca5ebfb5a44d4acdc83b3ed4b97d6
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07297704B2

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