Heptafluorobutyryl Chloride → Methyl (3-heptafluorobutyramido-4-hydroxyphenyl)acetate

HRID 48162

반응식

HRID 48162 반응식
C(=O)(O)[O-].[Na+].[CH3:6][O:7][C:8](=[O:18])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([NH2:17])[CH:11]=1.[F:19][C:20]([F:31])([C:27]([F:30])([F:29])[F:28])[C:21]([F:26])([F:25])[C:22](Cl)=[O:23]>COCCOC>[CH3:6][O:7][C:8](=[O:18])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([NH:17][C:22](=[O:23])[C:21]([F:25])([F:26])[C:20]([F:19])([F:31])[C:27]([F:30])([F:29])[F:28])[CH:11]=1

참가 물질

5

반응물 3

HCID 67810Heptafluorobutyryl ChlorideHCID 516892Sodium BicarbonateHCID 1475136Methyl 2-(3-amino-4-hydroxyphenyl)acetate

생성물 1

HCID 22742096Methyl (3-heptafluorobutyramido-4-hydroxyphenyl)acetate수율 72.1%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매3회

실험 절차

Sodium bicarbonate (51 g, 0.607 mol) was suspended in 1,2-dimethoxyethane (180 ml), and methyl(3-amino-4-hydroxyphenyl)acetate (58.26 g, 0.32 mol) was added, followed by a further quantity of 1,2-dimethoxyethane (75 ml). To this mixture was added, dropwise, a solution of heptafluorobutyryl chloride (112.5 g, 0.48 mol) in 1,2-dimethoxyethane (140 ml), at such a rate that the reaction temperature was maintained at 19-20° C. Once the addition was complete, the mixture was stirred at room temperature for 1½ hours. The reaction mixture was filtered and the solid was taken up in ethyl acetate and washed with saturated aqueous bicarbonate solution and brine. The organic phase was dried over anhydrous magnesium sulfate, filtered and the filtrate was evaporated in vacuo. The residue was taken up in acetone (450 ml) and water (450 ml) was added. The mixture was stirred for 1½ hours, during which time an oil separated. The aqueous acetone was decanted and a further quantity (250 ml) of water was added to the oil. The mixture was stirred for 1 hour, during which time the desired product crystallised; it was collected by filtration, washed with water and dried to give methyl(3-heptafluorobutyramido-4-hydroxyphenyl)acetate (87.0 g).

후처리

  1. additionTo this mixture was added
  2. additionOnce the addition
  3. filtrationThe reaction mixture was filtered
  4. washwashed with saturated aqueous bicarbonate solution and brine
  5. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe filtrate was evaporated in vacuo
  8. additionwater (450 ml) was added
  9. stirringThe mixture was stirred for 1½ hours, during which time an oil
  10. customseparated
  11. customThe aqueous acetone was decanted
  12. additiona further quantity (250 ml) of water was added to the oil
  13. stirringThe mixture was stirred for 1 hour, during which time the desired product
  14. customcrystallised
  15. filtrationit was collected by filtration
  16. washwashed with water
  17. customdried

출처 및 근거

ORD 기록
ord-49a98d68f8804cff9af8f96d3321c50b
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06703347B2

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