Diethyl Ether → HCID 58002946, compound

HRID 1516682Notes

Reaction equation

HRID 1516682 reaction equation
[CH3:1][C:2]1[O:17][C:7]2[CH:8]=[C:9]3[O:16][CH:15]=[CH:14][C:10]3=[C:11]([O:12][CH3:13])[C:6]=2[C:4](=[O:5])[CH:3]=1.[CH2:18](OCC)C.C[Al](C)C.[K].C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[Na+]>C(OCC)(=O)C.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.[Ni+2].O1CCCC1>[CH3:13][O:12][C:11]1[C:10]2[CH:14]=[CH:15][O:16][C:9]=2[CH:8]=[C:7]2[C:6]=1[C:4](=[O:5])[CH2:3][C:2]([CH3:18])([CH3:1])[O:17]2

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 6716VisnaginHCID 16682925TrimethylaluminumHCID 86636910CID 86636910

Product 1

HCID 58002946HCID 58002946, compound

Reagents, catalysts & solvents 3

HCID 9834912Nickel(II) acetylacetonateCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-20 °C

Procedure

Under argon, 25 g of visnagin (108.6 mmol) are suspended in 500 ml of abs. diethyl ether and 50 ml of abs. tetrahydrofuran, 2.23 g (8.7 mmol) of nickel(II) acetylacetonate are added and the mixture is cooled to −20° C. At this temperature, 81.44 ml (162.9 mmol) of trimethylaluminum (2 M solution in hexane) are added slowly, and the mixture is then slowly warmed to 0° C. and stirring is continued. After one hour, 500 ml of saturated potassium/sodium tartrate solution are added (vigorous evolution of gas), and the mixture is then diluted with 500 ml of ethyl acetate. The organic phase is separated off and the aqueous phase is extracted once more with ethyl acetate. The combined organic phases are washed twice with saturated sodium chloride solution, dried over sodium sulfate, filtered and evaporated to dryness. The residue is chromatographed on silica gel (mobile phase: cyclohexane/ethyl acetate 5:1). This gives 23.28 g (86% of theory) of the title compound.

Workup

  1. temperaturethe mixture is then slowly warmed to 0° C.
  2. customThe organic phase is separated off
  3. extractionthe aqueous phase is extracted once more with ethyl acetate
  4. washThe combined organic phases are washed twice with saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe residue is chromatographed on silica gel (mobile phase: cyclohexane/ethyl acetate 5:1)

Sources & evidence

ORD record
ord-10911a213588405ebe60ec718285db3a
Source dataset
uspto-grants-2012_07
Patent number
US08227511B2

Reaction notes

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