Dimethylformamide → 2-Propynyl 4-(2-propynyloxy)-3-methoxybenzoate

HRID 1675569ノート

反応式

HRID 1675569 の反応式
CN(C=O)C.[OH:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][C:8]=1[O:16][CH3:17].[CH2:18](Br)[C:19]#[CH:20].[C:22](=O)([O-])[O-].[K+].[K+].C(O[CH2:32][CH3:33])(=O)C>>[CH2:18]([O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([O:13][CH2:22][C:32]#[CH:33])=[O:12])=[CH:9][C:8]=1[O:16][CH3:17])[C:19]#[CH:20]

参加物

6

反応物 5

HCID 6228DimethylformamideHCID 7842Propargyl bromideHCID 8468Vanillic AcidHCID 8857Ethyl AcetateHCID 11430Potassium Carbonate

生成物 1

HCID 593017652-Propynyl 4-(2-propynyloxy)-3-methoxybenzoate

実験手順

To 100 ml of DMF were added 10 g of 4-hydroxy-3-methoxybenzoic acid, 15.7 g of propargyl bromide and 18 g of potassium carbonate, and the resulting mixture was stirred at room temperature for 8 hours, and then at 80° C. for 2 hours. Thereafter, ethyl acetate was added to the reaction mixture which had been allowed to cool to near room temperature, and this was filtered through Celite (registered trade mark). To the filtrate were added sequentially water and dilute hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was dried with magnesium sulfate, and concentrated under reduced pressure. The resulting crystals were washed with a mixed solvent of hexane and MTBE, and 13.2 g of 2-propynyl 4-(2-propynyloxy)-3-methoxybenzoate was obtained.

後処理

  1. waitat 80° C. for 2 hours
  2. temperatureto cool to near room temperature
  3. filtrationthis was filtered through Celite (registered trade mark)
  4. additionTo the filtrate were added sequentially water and dilute hydrochloric acid
  5. extractionfollowed by extraction with ethyl acetate
  6. dry with materialThe organic layer was dried with magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. washThe resulting crystals were washed with a mixed solvent of hexane and MTBE

出典と根拠

ORDレコード
ord-d9dc0ac6b2374d3d99b18afd6c4ca319
出典データセット
uspto-grants-2011_08
特許番号
US08003699B2

反応ノート

読み込み中…