Diethyl Ether → HCID 13300907, compound

HRID 1111483Notes

Reaction equation

HRID 1111483 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[O:12]1[C@@H:22]2[C@H:13]1[CH2:14][C:15](=[CH2:28])[CH:16]=[CH:17][C@H:18]([CH:25]([CH3:27])[CH3:26])[CH2:19][CH:20]([OH:24])[C:21]2=[O:23].CCOCC>C(Cl)Cl.CCCCCC.C(OCC)(=O)C>[O:12]1[C@@H:22]2[C@H:13]1[CH2:14][C:15](=[CH2:28])[CH:16]=[CH:17][C@H:18]([CH:25]([CH3:26])[CH3:27])[CH2:19][C:20](=[O:24])[C:21]2=[O:23]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 13845284HCID 13845284, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 13300907HCID 13300907, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 21226206Ethyl acetate hexaneSolvent

Procedure

100 mg of pyridinium chlorochromate and 200 mg of Molecular Sieves 3A were suspended in 6 ml of dry methylene chloride. While the suspension was cooled with ice and stirred, a solution of 50 mg of the product obtained in step 5, in a small amount of methylene chloride, was added. The temperature was elevated to room temperature, and the reaction mixture was allowed to react for 6 hours under vigorous agitation. After 10 ml of ether were added to the reaction mixture, the mixture was filtered using 15 g of "Florisil", and the precipitate and the "Florisil" were washed well with ether. The filtrate and the washing solution were combined and were evaporated to dryness to provide a crude product. Using n-hexane-ethyl acetate as an eluent, the crude product was subjected to column chromatography using 3 g of alumina (activity: II). The fraction which eluted with n-hexane-ethyl acetate (99:1) was recovered and was evaporated to dryness to provide 42 mg of purified (3S,4E,8R,9R)-8-epoxy-3-isopropyl-6-methylene-10-oxo-4-cyclodecen-1-one (the compound of formula 8). The yield was 85%.

Workup

  1. temperatureWhile the suspension was cooled with ice
  2. customwas elevated to room temperature
  3. customto react for 6 hours under vigorous agitation
  4. filtrationthe mixture was filtered
  5. washthe precipitate and the "Florisil" were washed well with ether
  6. customwere evaporated to dryness
  7. customto provide a crude product
  8. washThe fraction which eluted with n-hexane-ethyl acetate (99:1)
  9. customwas recovered
  10. customwas evaporated to dryness

Sources & evidence

ORD record
ord-3276c30c00554e73aebb6f19f7551657
Source dataset
uspto-grants-1990_12
Patent number
US04980485

Reaction notes

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