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

HRID 2236365ノート

反応式

HRID 2236365 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

反応条件

温度
80 °C

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 mixture obtained was stirred at room temperature for 8 hours and at 80° C. for 2 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 13.2 g of 2-propynyl 4-(2-propynyloxy)-3-methoxybenzoate represented by the formula:

後処理

  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

出典と根拠

ORDレコード
ord-0ff7d27c011542409e8f673951e2988f
出典データセット
uspto-grants-2010_05
特許番号
US07714168B2

反応ノート

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