Toluene → HCID 22600462、化合物

HRID 1367685ノート

反応式

HRID 1367685 の反応式
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

参加物

7

反応物 4

HCID 1140TolueneHCID 81531DiisopropylethylamineHCID 113349532-(2-Methoxy-ethoxymethyl)-6-trifluoromethyl-nicotinic acidHCID 57591516HCID 57591516、化合物

生成物 1

HCID 22600462HCID 22600462、化合物

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6192e180938442a3a666152bcb3cb5a8
出典データセット
uspto-grants-2011_02
特許番号
US07893270B2

反応ノート

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