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

HRID 1093971ノート

反応式

HRID 1093971 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 stirring 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. stirringAfter stirring 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-9611921183b94692b933aec6ea2190ee
出典データセット
uspto-grants-2012_03
特許番号
US08133889B2

反応ノート

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