Potassium Carbonate → Methyl 3,4-dimethoxy-5-(2-propynyloxy)benzoate

HRID 34460

반응식

HRID 34460 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([OH:15])[C:12]=1[O:13][CH3:14])[C:6]([O:8][CH3:9])=[O:7].[CH2:16](Cl)[C:17]#[CH:18].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.[I-].[Na+]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([O:15][CH2:18][C:17]#[CH:16])[C:12]=1[O:13][CH3:14])[C:6]([O:8][CH3:9])=[O:7]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 122213-Chloro-1-propyneHCID 2733956Methyl 3-hydroxy-4,5-dimethoxybenzoate

생성물 1

HCID 12849835Methyl 3,4-dimethoxy-5-(2-propynyloxy)benzoate수율 49%

시약·촉매·용매 2

HCID 5238Sodium Iodide촉매HCID 180Acetone용매

실험 절차

Methyl 3,4-dimethoxy-5-hydroxybenzoate (E. Spath and H. Roder, Mon. f. Chem. 1922, 43, 93; G. J. Kapadia, Y. N. Vaishnav, M. B. E. Fayez, J. Pharm. Sci. 1969, 9, 1157) (0.54 g, 2.54 mmol), propargyl chloride (0.23 g, 3.04 mmol), sodium iodide (3 mg, 0.02 mmol) and potassium carbonate (0.53 g, 3.81 mmol) were refluxed in acetone (10 mL) for 18 hr, cooled, filtered and concentrated. The resulting oil was dissolved in ethyl acetate (20 mL) and washed with water (3×10 mL). The organic layer was dried (Na2SO4), concentrated and recrystllized from alcohol (2.5 mL)/hexane (20 mL) to give methyl 3,4-dimethoxy-5-(2-propynyloxy)benzoate (0.29 g, 49%); mp 72°-73.5°. Anal. Calcd for C13H14O5 : C, 62.39; H, 5.64. Found: C, 62.28; H, 5.68.

후처리

  1. temperaturecooled
  2. filtrationfiltered
  3. concentrationconcentrated
  4. dissolutionThe resulting oil was dissolved in ethyl acetate (20 mL)
  5. washwashed with water (3×10 mL)
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-287d059925c14d72ad4bbfea83bf529e
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04761475

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