Potassium Carbonate → Ethyl 7-(4-chlorophenyl)-2,3-dihydro-1-benzoxepine-4-carboxylate

HRID 566005노트

반응식

HRID 566005 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH2:10][CH2:9][C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7][C:6]=2[CH:17]=1.B([O-])([O-])O[C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C(CCO)=CC=CC=1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([C:2]2[CH:3]=[CH:4][C:5]3[O:11][CH2:10][CH2:9][C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7][C:6]=3[CH:17]=2)=[CH:21][CH:22]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 10709089HCID 10709089, 화합물HCID 867561664-Chlorophenyl borate

생성물 1

HCID 18472211Ethyl 7-(4-chlorophenyl)-2,3-dihydro-1-benzoxepine-4-carboxylate수율 83%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 66602552Toluene-ethanol water용매

실험 절차

Under argon atmosphere, a solution of ethyl 7-bromo-2,3-dihydro-1-benzoxepine-4-carboxylate (500 mg), 4-chloro-phenyl borate (289 mg) and potassium carbonate (464 mg) in toluene-ethanol-water (20-2-2 ml) was stirred at room temperature for 1 hour. To the reaction mixture was added tetrakistriphenyl-phosphinepalladium (0.06 g), and the mixture was refluxed for 24 hours and cooled to room temperature. The organic layer was washed with saturated sodium chloride solution, dried with magnesium sulfate and concentrated under reduced pressure. The residue was -separated and purified with column chromatography (ethyl acetate/hexane=1:19) to give ethyl 7-(4-chlorophenyl)-2,3-dihydro-1-benzoxepine-4-carboxylate (459 mg) as colorless crystals.

후처리

  1. temperaturethe mixture was refluxed for 24 hours
  2. washThe organic layer was washed with saturated sodium chloride solution
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. custompurified with column chromatography (ethyl acetate/hexane=1:19)

출처 및 근거

ORD 기록
ord-7011ec28387c466c91a796faa29b2d39
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06172061B2

반응 노트

불러오는 중…