Toluene → HCID 22600462, 화합물

HRID 1784150노트

반응식

HRID 1784150 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, (Preparation Example P2) 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 under a nitrogen atmosphere at room temperature until a clear brown solution having a white sediment is formed. The reaction mixture is then maintained under moderate reflux for 26 hours in an oil bath, with stirring. 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) and 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 vacuo, 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. temperatureThe reaction mixture is then maintained
  3. temperatureunder moderate reflux for 26 hours in an oil bath
  4. stirringwith stirring
  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 vacuo, 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-e08e1cbc6beb424492820e89b8e50368
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07501544B2

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