Acetone → ACMC-20apjz

HRID 1659008Notes

Reaction equation

HRID 1659008 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].O>[B-](F)(F)(F)F.[Ag+].CO>[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

6

Reactant 3

HCID 180AcetoneHCID 962WaterHCID 130462774-Bromo-2-(6-carboxyhexyl)cyclopent-2-en-1-one

Product 1

HCID 3690897ACMC-20apjz

Reagents, catalysts & solvents 2

HCID 159722Silver tetrafluoroborateCatalystHCID 887MethanolSolvent

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 93) in 100 ml. of acetone and 65 ml. of water is added 8.80 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 ether. The extract is extracted with half saturated sodium bicarbonate solutions. The basic solutions 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; λmax.MeOH = 233 mμ. (7360); νmax. = 3380 (hydroxyl groups), 1710 (carbonyl groups), and 1632 cm-1 (olefin group).

Workup

  1. temperatureThe temperature is maintained at 25°-30°C. by external cooling
  2. filtrationfiltered, saturated with sodium chloride
  3. extractionextracted with ether
  4. extractionThe extract is extracted with half saturated sodium bicarbonate solutions
  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

Sources & evidence

ORD record
ord-6e33ba77a2d843c68c99debad813e1a2
Source dataset
uspto-grants-1976_06
Patent number
US03966773

Reaction notes

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