Potassium Carbonate → Ethyl 4-[(4-bromophenyl)thio]-3-oxocyclohexanecarboxylate

HRID 1593642ノート

反応式

HRID 1593642 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH:16]1[CH2:21][CH2:20][CH:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:18][C:17]1=[O:27]>CC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:16]2[CH2:21][CH2:20][CH:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:18][C:17]2=[O:27])=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 660494-BromothiophenolHCID 12917736Ethyl 4-bromo-3-oxocyclohexanecarboxylate

生成物 1

HCID 69249727Ethyl 4-[(4-bromophenyl)thio]-3-oxocyclohexanecarboxylate収率 63.4%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒2 回

実験手順

To a solution of 4-bromobenzenethiol (2.92 g, 15.45 mmol) in 20 mL acetone was added K2CO3 (2.2 g, 15.18 mmol) and a solution of ethyl 4-bromo-3-oxocyclohexanecarboxylate (3.73 g, 15 mmol) in acetone (10 mL). The resulting suspension was stirred at room temperature for 2 hour, and then was partitioned between water and hexane. The organic layer was washed with water, then brine, then was dried over MgSO4, filtered, and concentrated. Purification by chromatography on silica gel (15% EtOAc in hexane) afforded 3.4 g (61%) of the title compound as an oil: MS (ES) m/z=356 [M]+.

後処理

  1. customwas partitioned between water and hexane
  2. washThe organic layer was washed with water
  3. dry with materialbrine, then was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by chromatography on silica gel (15% EtOAc in hexane)

出典と根拠

ORDレコード
ord-777c705b79ad4b9abdb9db43c20725ea
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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