Dimethylformamide → 2-Propynyl 4-(2-propynyloxy)-3,5-dimethoxybenzoate

HRID 602010노트

반응식

HRID 602010 반응식
CN(C=O)C.[OH:6][C:7]1[C:15]([O:16][CH3:17])=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][C:8]=1[O:18][CH3:19].[CH2:20](Br)[C:21]#[CH:22].[C:24](=O)([O-])[O-].[K+].[K+].C(O[CH2:34][CH3:35])(=O)C>>[CH2:20]([O:6][C:7]1[C:8]([O:18][CH3:19])=[CH:9][C:10]([C:11]([O:13][CH2:24][C:34]#[CH:35])=[O:12])=[CH:14][C:15]=1[O:16][CH3:17])[C:21]#[CH:22]

참가 물질

6

반응물 5

HCID 6228DimethylformamideHCID 7842Propargyl bromideHCID 8857Ethyl AcetateHCID 10742Syringic AcidHCID 11430Potassium Carbonate

생성물 1

HCID 593017922-Propynyl 4-(2-propynyloxy)-3,5-dimethoxybenzoate

반응 조건

온도
80 °C

실험 절차

To 100 ml of DMF were added 11.8 g of 4-hydroxy-3,5-dimethoxybenzoic acid, 15.7 g of propargyl bromide and 18 g of potassium carbonate, and the mixture obtained was stirred at room temperature for 8 hours and at 80° C. for 4 hours. Then, ethyl acetate was added to the reaction mixture and the mixture was filtered through Celite. Water and dilute hydrochloric acid were added to the filtrate in order and it was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The crystals obtained were washed with a mix solvent of hexane and MTBE to obtain 15.5 g of 2-propynyl 4-(2-propynyloxy)-3,5-dimethoxybenzoate represented by the formula:

후처리

  1. customthe mixture obtained
  2. filtrationthe mixture was filtered through Celite
  3. additionWater and dilute hydrochloric acid were added to the filtrate in order and it
  4. extractionwas extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crystals obtained
  8. washwere washed with a mix solvent of hexane and MTBE

출처 및 근거

ORD 기록
ord-12a19def90b94d59947f5b5395ea1010
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902400B2

반응 노트

불러오는 중…