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

HRID 1593642노트

반응식

HRID 1593642 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매2회

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-777c705b79ad4b9abdb9db43c20725ea
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07297704B2

반응 노트

불러오는 중…