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

HRID 480158노트

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HRID 480158 반응식
[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]

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 6451Bromocresol GreenHCID 65578Oxalyl chlorideHCID 110420624-(Methoxycarbonyl)bicyclo[2.2.2]octane-1-carboxylic acid2회

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 21226129Dichloromethane methanol용매

실험 절차

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., taking 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 45°, 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.

후처리

  1. additionthe resulting mixture is added to the mixture
  2. customThe solvent is removed under reduced pressure at 40 to 45°
  3. additiondichloromethane (5 vol) is 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

출처 및 근거

ORD 기록
ord-4b0bf71f93fd433c95b3fb013b16ea02
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06649600B1

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