Pyridine → HCID 56626471, compound

HRID 261868Notes

Reaction equation

HRID 261868 reaction equation
OC1C2[C@@H]3CC(=NO)CC[C@H]3C(C)(C)OC=2C=C(C(C)(C)CCCCCC)C=1.C(OC(=O)C)(=O)C.N1C=CC=CC=1.[C:42]([O:45][C:46]1[C:55]2[CH:54]3[CH2:56][C:57]([N:60]([C:64](=[O:66])[CH3:65])[C:61](=[O:63])[CH3:62])=[CH:58][CH2:59][CH:53]3[C:52]([CH3:68])([CH3:67])[O:51][C:50]=2[CH:49]=[C:48]([C:69]([CH3:77])([CH3:76])[CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH3:75])[CH:47]=1)(=[O:44])[CH3:43]>O.C(OCC)C>[C:42]([O:45][C:46]1[C:55]2[C@@H:54]3[CH2:56][C:57]([N:60]([C:64](=[O:66])[CH3:65])[C:61](=[O:63])[CH3:62])=[CH:58][CH2:59][C@H:53]3[C:52]([CH3:67])([CH3:68])[O:51][C:50]=2[CH:49]=[C:48]([C:69]([CH3:76])([CH3:77])[CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH3:75])[CH:47]=1)(=[O:44])[CH3:43]

Participants

7

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 20346209HCID 20346209, compoundHCID 86736513HCID 86736513, compound

Product 1

HCID 56626471HCID 56626471, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 2.59 g. of dl-trans-1-hydroxy-3-(1,1-dimethylheptyl)-6,6-dimethyl-9-hydroxyimino-6a,7,8,9,10,10a-hexahydro-6H-dibenzo[b,d]pyran in 25 ml. of acetic anhydride and 75 ml. of pyridine was stirred under a nitrogen gas atmosphere and heated to reflux for twenty-four hours. After cooling the reaction mixture to room temperature, the solvent was removed therefrom by evaporation under reduced pressure to provide an oily residue. The residue was dissolved in 50 ml. of diethylether and 50 ml. of water and stirred for one hour. The mixture was filtered and the organic layer was separated. The ethereal solution was washed with 1 N hydrochloric acid, water, saturated sodium chloride solution and dried. Removal of the solvent afforded 3.57 g. of a dark oil which was then chromatographed over 100 g. of Woelm Activity I silica gel, eluting with fifty percent hexane-diethyl ether. The fractions containing the major product were combined and concentrated to dryness to provide 3.12 g. of predominantly dl-1-acetoxy-3-(1,1-dimethylheptyl)-6,6-dimethyl-9-(N,N-diacetylamino)-6a,7,10,10a-tetrahydro-6H-dibenzo[b,d]pyran, with a minor quantity of the Δ9 compound.

Workup

  1. temperatureheated
  2. temperatureto reflux for twenty-four hours
  3. customthe solvent was removed
  4. customby evaporation under reduced pressure
  5. customto provide an oily residue
  6. dissolutionThe residue was dissolved in 50 ml
  7. filtrationThe mixture was filtered
  8. customthe organic layer was separated
  9. washThe ethereal solution was washed with 1 N hydrochloric acid, water, saturated sodium chloride solution
  10. customdried
  11. customRemoval of the solvent
  12. customafforded 3.57 g
  13. customof a dark oil which was then chromatographed over 100 g
  14. washof Woelm Activity I silica gel, eluting with fifty percent hexane-diethyl ether
  15. additionThe fractions containing the major product
  16. concentrationconcentrated to dryness
  17. customto provide 3.12 g

Sources & evidence

ORD record
ord-cd8d28963d0143edb9d5ee323c04b775
Source dataset
uspto-grants-1979_05
Patent number
US04152450

Reaction notes

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