Acetone → ACMC-20apjz

HRID 617067Notes

Reaction equation

HRID 617067 reaction equation
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]

Participants

5

Reactant 2

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

Product 1

HCID 3690897ACMC-20apjz

Reagents, catalysts & solvents 2

HCID 159722Silver tetrafluoroborateCatalystHCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-fd7828418f3e48418426f983ab0af236
Source dataset
uspto-grants-1978_02
Patent number
US04076947

Reaction notes

Loading…