Sodium Carbonate → HCID 67517443、化合物

HRID 1519508ノート

反応式

HRID 1519508 の反応式
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[C:12]1[CH:13]=[C:14]([CH2:18][C:19](O)=[O:20])[CH:15]=[CH:16][CH:17]=1.[C:22](Cl)(=O)[C:23](Cl)=O.[Cl-].[Al+3].[Cl-].[Cl-].C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl.CN(C=O)C>[O:20]=[C:19]1[CH2:18][C:14]2[CH:13]=[C:12]([N:3]3[C:2](=[O:1])[C:10]4[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=4)[C:4]3=[O:11])[CH:17]=[CH:16][C:15]=2[CH2:23][CH2:22]1

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 212622833-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)benzeneacetic acid

生成物 1

HCID 67517443HCID 67517443、化合物

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of [3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)phenyl]acetic acid (0.75 g, 2.7 mmol) in DCM (25 mL) was added oxalyl chloride (0.28 mL, 3.2 mmol) and a drop of DMF. The mixture was allowed to stir at RT until all solids disappeared. At that point, the solution was cooled to to 0° C. with an ice bath, and aluminum chloride (1.1 g, 8.0 mmol) was added into the reaction slowly. After stirring the mixture for another 10 minutes, ethylene was bubbled through the reaction via a long needle. TLC showed complete reaction within 30 minutes. The reaction was poured into ice water, neutralized with sodium carbonate, extracted with DCM, dried, concentrated, and purified by MPLC (Hexane/EtOAc). LC-MS (IE, m/z): 292 [M+1]+.

後処理

  1. temperatureAt that point, the solution was cooled to to 0° C. with an ice bath
  2. stirringAfter stirring the mixture for another 10 minutes
  3. customethylene was bubbled through the reaction via a long needle
  4. customreaction within 30 minutes
  5. extractionextracted with DCM
  6. customdried
  7. concentrationconcentrated
  8. custompurified by MPLC (Hexane/EtOAc)

出典と根拠

ORDレコード
ord-d9ca84ab0442408ebd5d18e79742e674
出典データセット
uspto-grants-2015_07
特許番号
US09073882B2

反応ノート

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