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

HRID 1593614ノート

反応式

HRID 1593614 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].[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

参加物

5

反応物 3

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

生成物 1

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

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 (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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-cb0ca5ebfb5a44d4acdc83b3ed4b97d6
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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