HCID 131711211, compound → HCID 20311444, compound

HRID 2420272Notes

Reaction equation

HRID 2420272 reaction equation
[C:1]1(=[O:12])[C:10]2[CH:5]([CH2:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH2:3][CH2:2]1.[CH2:13]=[CH:14][CH:15]1[CH2:20][CH:19]=[CH:18][CH2:17][CH2:16]1>C1COCC1.N12CCCC1=NCCC2.C1C=CC=CC=1>[CH2:17]([C:16]1[C:2]2[C:1](=[O:12])[C:10]3[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=3[C:4](=[O:11])[C:3]=2[CH:13]=[CH:14][CH:15]=1)[CH2:18][CH:19]=[CH2:20]

Participants

5

Reactant 1

HCID 131711211HCID 131711211, compound

Product 1

HCID 20311444HCID 20311444, compoundYield 34%

Reagents, catalysts & solvents 3

HCID 763491,5-Diazabicyclo(4.3.0)non-5-eneCatalystHCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A 45 g sample of the tetrahydronaphthoquinone-butadiene dimer adduct of Example 1 was dissolved in 400 ml THF and 20 drops of 1,5-diazabicyclo[4.3.0]non-5-ene were added. The solution was stirred for 65 hours while exposed to air. The THF was then blown off with air and the residue was dissolved in benzene. The benzene solution was filtered to remove insoluble impurities and the solution was then chromatographed on Florisil. The product was eluted with a 4:1 mixture of benzene/ethyl acetate, and the yield of crude product was 15 g (34% yield). An analytical sample, after recrystallization first from ethanol, then from hexane, had a mp of 111° to 113° C.

Workup

  1. filtrationThe benzene solution was filtered
  2. customto remove insoluble impurities
  3. customthe solution was then chromatographed on Florisil
  4. washThe product was eluted with a 4:1 mixture of benzene/ethyl acetate
  5. customAn analytical sample, after recrystallization first from ethanol

Sources & evidence

ORD record
ord-492fae56f5fd44cbb5e8d1265ea5298a
Source dataset
uspto-grants-1978_08
Patent number
US04110353

Reaction notes

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