Acetone → ACMC-20apjz

HRID 261912

반응식

HRID 261912 반응식
Br[CH:2]1[CH2:6][C:5](=[O:7])[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:3]1.CC(C)=[O:19]>[B-](F)(F)(F)F.[Ag+].O>[C:14]([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:4]1[C:5](=[O:7])[CH2:6][CH:2]([OH:19])[CH:3]=1)([OH:16])=[O:15]

참가 물질

5

반응물 2

HCID 180AcetoneHCID 130462774-Bromo-2-(6-carboxyhexyl)cyclopent-2-en-1-one

생성물 1

HCID 3690897ACMC-20apjz

시약·촉매·용매 2

HCID 159722Silver tetrafluoroborate촉매HCID 962Water용매

실험 절차

To a stirred solution of 10.6 g. (ca. 34 mmoles) of crude 4-bromo-2-(6-carboxyhexyl)cyclopent-2-en-1-one (Example 8) in 100 ml. of acetone and 65 ml. of water is added 8.0 g. (45.2 mmoles) of silver fluoborate during 2 minutes. The temperature is maintained at 25°-30° C. by external cooling. The mixture is stirred for 90 minutes, filtered, saturated with sodium chloride and extracted with half saturated sodium bicarbonate solution. The basic extract is reacidified with dilute hydrochloric acid, saturated with sodium chloride, and extracted with ether. The extract is washed with water and saturated sodium chloride solution, dried over magnesium sulfate, and concentrated. The crude product is purified by partition chromatography on Celite to give an oil with the properties described in Example 27.

후처리

  1. temperatureThe temperature is maintained at 25°-30° C. by external cooling
  2. filtrationfiltered, saturated with sodium chloride
  3. extractionextracted with half saturated sodium bicarbonate solution
  4. extractionThe basic extract
  5. extractionextracted with ether
  6. washThe extract is washed with water and saturated sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe crude product is purified
  10. customby partition chromatography on Celite
  11. customto give an oil with the properties

출처 및 근거

ORD 기록
ord-fe90540513ff4433ae35360fde338743
출처 데이터셋
uspto-grants-1979_05
특허 번호
US04152524

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