Toluene → HCID 22600462, 화합물

HRID 1367685노트

반응식

HRID 1367685 반응식
Cl[C:2]1[CH:8]2[CH2:9][CH:5]([CH2:6][CH2:7]2)[C:4](=[O:10])[CH:3]=1.[CH3:11][O:12][CH2:13][CH2:14][O:15][CH2:16][C:17]1[N:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:18]=1[C:19]([OH:21])=[O:20].C(N(C(C)C)CC)(C)C.C1(C)C=CC=CC=1>[Cl-].[Cl-].[Zn+2].ClCCl>[CH3:11][O:12][CH2:13][CH2:14][O:15][CH2:16][C:17]1[C:18]([C:19]([O:21][C:2]2[CH:8]3[CH2:9][CH:5]([CH2:6][CH2:7]3)[C:4](=[O:10])[CH:3]=2)=[O:20])=[CH:22][CH:23]=[C:24]([C:26]([F:29])([F:27])[F:28])[N:25]=1

참가 물질

7

반응물 4

HCID 1140TolueneHCID 81531DiisopropylethylamineHCID 113349532-(2-Methoxy-ethoxymethyl)-6-trifluoromethyl-nicotinic acidHCID 57591516HCID 57591516, 화합물

생성물 1

HCID 22600462HCID 22600462, 화합물

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 6344Dichloromethane용매

실험 절차

A mixture of 200 mg (1.15 mmol) of 4-chlorobicyclo[3.2.1]oct-3-en-2-one, 16 mg (0.12 mmol) of ZnCl2, 324 mg (1.15 mmol) of 2-methoxyethoxymethyl-6-trifluoromethylnicotinic acid, 166 mg (1.27 mmol) of diisopropylethylamine and 5 ml of toluene is stirred at room temperature under a nitrogen atmosphere until a clear brown solution having a white sediment is formed. With stirring, the reaction mixture is then maintained under moderate reflux for 26 hours in an oil bath. The reaction mixture is then cooled to ambient temperature and 30 ml of dichloromethane are added. The solution is then washed twice with water (20 ml each time), then twice with 0.1M hydrochloric acid (20 ml each time) and again twice with water (15 ml each time). After drying the organic solution using magnesium sulfate and concentrating in vacuum, 284 mg of 4-(2-methoxyethoxymethyl-6-trifluoromethyl-pyridin-3-ylcarbonyloxy)-bicyclo[3.2.1]oct-3-en-2-one are obtained in the form of a brown oil.

후처리

  1. customis formed
  2. stirringWith stirring
  3. temperaturethe reaction mixture is then maintained
  4. temperatureunder moderate reflux for 26 hours in an oil bath
  5. temperatureThe reaction mixture is then cooled to ambient temperature
  6. washThe solution is then washed twice with water (20 ml each time)
  7. customAfter drying the organic solution
  8. concentrationconcentrating in vacuum, 284 mg of 4-(2-methoxyethoxymethyl-6-trifluoromethyl-pyridin-3-ylcarbonyloxy)-bicyclo[3.2.1]oct-3-en-2-one
  9. customare obtained in the form of a brown oil

출처 및 근거

ORD 기록
ord-6192e180938442a3a666152bcb3cb5a8
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07893270B2

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