Dimethylformamide → Bicyclo[2.2.2]octane-1-carboxylic acid, 4-(chlorocarbonyl)-, methyl ester

HRID 2105682ノート

反応式

HRID 2105682 の反応式
[CH3:1][O:2][C:3]([C:5]12[CH2:12][CH2:11][C:8]([C:13]([OH:15])=O)([CH2:9][CH2:10]1)[CH2:7][CH2:6]2)=[O:4].CN(C)C=O.C(Cl)(=O)C([Cl:24])=O.CC1C(Br)=C(O)C(Br)=CC=1C1(C2C=C(Br)C(O)=C(Br)C=2C)OS(=O)(=O)C2C=CC=CC1=2>ClCCl.ClCCl.CO>[CH3:1][O:2][C:3]([C:5]12[CH2:12][CH2:11][C:8]([C:13]([Cl:24])=[O:15])([CH2:9][CH2:10]1)[CH2:7][CH2:6]2)=[O:4]

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 6451Bromocresol GreenHCID 65578Oxalyl chlorideHCID 110420624-(Methoxycarbonyl)bicyclo[2.2.2]octane-1-carboxylic acid2 回

生成物 1

HCID 13761775Bicyclo[2.2.2]octane-1-carboxylic acid, 4-(chlorocarbonyl)-, methyl ester

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 21226129Dichloromethane methanol溶媒

実験手順

Bicyclo-[2.2.2]octane-1,4-dicarboxylic acid monomethyl ester (IV, Example 81, 1 wt) is dissolved in dichloromethane (6.25 vol) and dimethylformamide (0.025 vol) is added. Concomitantly oxalyl chloride (0.5125 vol) is dissolved in dichloromethane (0.625 vol) and the resulting mixture is added to the mixture containing the bicyclo [2.2.2]octane-1,4-dicarboxylic acid monomethyl ester (IV) at between 12 to 17° C., tag care for gas evolution. The mixture is stirred at 15 to 25° for 2 to 4 hours which is monitored by (TLC; dichloromethane/methanol: 9/1, visualization Bromocresol green). The solvent is removed under reduced pressure at 40 to 450, dichloromethane (5 vol) is added stirred for 5 to 15 min and removed under reduced pressure at 40 to 45°. The process is repeated by adding dichloromethane (5 vol), stirring for 5 to 15 min and removing under reduced pressure at 40 to 45°. Acetonitrile (6.25 vol) is then added to give the title compound in solution.

後処理

  1. additionthe resulting mixture is added to the mixture
  2. customThe solvent is removed under reduced pressure at 40 to 450, dichloromethane (5 vol)
  3. additionis added
  4. stirringstirred for 5 to 15 min
  5. customremoved under reduced pressure at 40 to 45°
  6. additionby adding dichloromethane (5 vol)
  7. stirringstirring for 5 to 15 min
  8. customremoving under reduced pressure at 40 to 45°
  9. additionAcetonitrile (6.25 vol) is then added

出典と根拠

ORDレコード
ord-8a651e1037764b6f81d26cad6b89c61f
出典データセット
uspto-grants-2009_08
特許番号
US07579354B2

反応ノート

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