Dimethylformamide → 5-[(morpholin-4-yl)methyl]-1H-pyrrole-2-carbaldehyde

HRID 241706ノート

反応式

HRID 241706 の反応式
CN([CH:4]=[O:5])C.O=P(Cl)(Cl)Cl.[NH:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[CH2:16][N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.C([O-])(=O)C.[K+].[OH-].[Na+]>C(Cl)Cl>[N:17]1([CH2:16][C:12]2[NH:11][C:15]([CH:4]=[O:5])=[CH:14][CH:13]=2)[CH2:18][CH2:19][O:20][CH2:21][CH2:22]1

参加物

7

反応物 5

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 517044Potassium AcetateHCID 66636594HCID 66636594、化合物

生成物 1

HCID 824012075-[(morpholin-4-yl)methyl]-1H-pyrrole-2-carbaldehyde

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
40 °C

実験手順

To a solution of DMF (18.04 mmoles) in DCM (10 ml) there is added POCl3, dropwise, at 0° C. After stirring for 5 minutes, a solution of the compound obtained in Step A (9.02 mmoles) is added dropwise. After stiffing for 3 hours at 0° C., the reaction mixture is heated at 40° C. for 30 minutes. At ambient temperature, an aqueous solution of potassium acetate (32 mmoles) is added and then the reaction mixture is stirred at 40° C. for 30 minutes. At ambient temperature, the solution is brought to alkaline pH using 2M NaOH solution and is then extracted with DCM. The organic phase is washed with water and with saturated NaCl solution, dried over sodium sulphate, filtered and evaporated to dryness. The residue obtained is purified on silica gel (SiO2; gradient DCM/AcOEt) to yield the title product.

後処理

  1. customat 0° C
  2. waitAfter stiffing for 3 hours at 0° C.
  3. stirringthe reaction mixture is stirred at 40° C. for 30 minutes
  4. customAt ambient temperature
  5. extractionis then extracted with DCM
  6. washThe organic phase is washed with water and with saturated NaCl solution
  7. dry with materialdried over sodium sulphate
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customThe residue obtained
  11. customis purified on silica gel (SiO2; gradient DCM/AcOEt)

出典と根拠

ORDレコード
ord-3ceaa16af83f475a96ac75a707c92cbe
出典データセット
uspto-grants-2014_02
特許番号
US08653073B2

反応ノート

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