Calcium Carbonate → HCID 13300898, compound

HRID 845141Notes

Reaction equation

HRID 845141 reaction equation
[CH:1]([C@@H:4]1[CH2:5][CH2:6][C:7](=[O:23])[CH:8](S(C2C=CC=CC=2)=O)[CH2:9][CH2:10][C:11](=[CH2:14])[CH:12]=[CH:13]1)([CH3:3])[CH3:2].C(=O)([O-])[O-].[Ca+2]>C1(C)C=CC=CC=1>[CH:1]([C@@H:4]1[CH2:5][CH2:6][C:7](=[O:23])[CH:8]=[CH:9][CH2:10][C:11](=[CH2:14])[CH:12]=[CH:13]1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 10112Calcium CarbonateHCID 13845280HCID 13845280, compound

Product 1

HCID 13300898HCID 13300898, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

After dissolving 2.6 g of the product of step 2 in 200 ml of toluene, 2.5 g of calcium carbonate were added to the solution and the mixture was refluxed under nitrogen gas stream for 5 hours. The reaction mixture was filtered to remove calcium carbonate, and the filtrate was concentrated under reduced pressure to 5 ml. Then, 10 ml of hexane were added to the concentrate. Using n-hexane-ethyl acetate as an eluent, the mixture was subjected to column chromatography using 100 g of alumina (activity: II). The fraction which eluted with n-hexane-ethyl acetate (95:5) was recovered and was evaporated to dryness to provide 760 mg of purified (8S,2Z,6E)-8-isopropyl-5-methylene-2,6-cyclodecadiene-1-one. The yield was 47%.

Workup

  1. additionwere added to the solution
  2. temperaturethe mixture was refluxed under nitrogen gas stream for 5 hours
  3. filtrationThe reaction mixture was filtered
  4. customto remove calcium carbonate
  5. concentrationthe filtrate was concentrated under reduced pressure to 5 ml
  6. additionThen, 10 ml of hexane were added to the concentrate
  7. washThe fraction which eluted with n-hexane-ethyl acetate (95:5)
  8. customwas recovered
  9. customwas evaporated to dryness

Sources & evidence

ORD record
ord-244402afef894173b27efd770fa7bb4b
Source dataset
uspto-grants-1988_07
Patent number
US04755626

Reaction notes

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