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

HRID 1675569노트

반응식

HRID 1675569 반응식
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]

참가 물질

6

반응물 5

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

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d9dc0ac6b2374d3d99b18afd6c4ca319
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08003699B2

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