Diisopropylethylamine → HCID 22600462、化合物

HRID 1784152ノート

反応式

HRID 1784152 の反応式
Br[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].CCN(C(C)C)C(C)C>ClC1C=CC=CC=1.[Cl-].[Cl-].[Zn+2]>[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

6

反応物 3

HCID 81531Diisopropylethylamine2 回HCID 113349532-(2-Methoxy-ethoxymethyl)-6-trifluoromethyl-nicotinic acid2 回HCID 57591513HCID 57591513、化合物

生成物 1

HCID 22600462HCID 22600462、化合物

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒2 回HCID 7964Chlorobenzene溶媒

実験手順

A mixture of 27 g of a 6.2% solution of 4-bromobicyclo[3.2.1]oct-3-en-2-one (Preparation Example P1) in chlorobenzene, 110 mg of ZnCl2, 2.34 g of 2-methoxyethoxymethyl-6-trifluoromethylnicotinic acid and 1.2 g of Hünig's base is stirred at room temperature under a nitrogen atmosphere until a dark-brown solution is formed. The reaction mixture is then maintained under moderate reflux for 19 hours in an oil bath, with stirring. The mixture is then divided into 2 portions. To one portion there are added a further 1.12 g of 2-methoxyethoxymethyl-6-trifluoromethylnicotinic acid, 0.06 g of ZnCl2 and 0.6 g of Hünig's base. The reaction mixture is then maintained under moderate reflux for 12 hours in an oil bath, with stirring. The solution is then washed twice with 0.1M hydrochloric acid (20 ml each time) and twice with water (20 ml each time). After drying the organic solution using magnesium sulfate and concentrating in vacuo, 3.9 g 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. temperatureThe reaction mixture is then maintained
  3. temperatureunder moderate reflux for 19 hours in an oil bath
  4. stirringwith stirring
  5. temperatureThe reaction mixture is then maintained
  6. temperatureunder moderate reflux for 12 hours in an oil bath
  7. stirringwith stirring
  8. washThe solution is then washed twice with 0.1M hydrochloric acid (20 ml each time) and twice with water (20 ml each time)
  9. customAfter drying the organic solution
  10. concentrationconcentrating in vacuo, 3.9 g of 4-(2-methoxyethoxymethyl-6-trifluoromethyl-pyridin-3-ylcarbonyloxy)-bicyclo[3.2.1]oct-3-en-2-one
  11. customare obtained in the form of a brown oil

出典と根拠

ORDレコード
ord-490092c910054855818fdd351ad58b33
出典データセット
uspto-grants-2009_03
特許番号
US07501544B2

反応ノート

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