Trifluoroacetic acid → 6,7,10,11,12-Pentamethoxy-3a,4,13,13a-tetrahydrodibenzo[4,5:6,7]cycloocta[1,2-c]furan-1(3H)-one

HRID 2351821Notes

Reaction equation

HRID 2351821 reaction equation
FC(F)(F)C(O)=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[CH3:21][O:22][C:23]1[C:46]([O:47][CH3:48])=[C:45]([O:49][CH3:50])[CH:44]=[CH:43][C:24]=1[CH2:25][CH:26]1[CH:31]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[C:35]([O:41][CH3:42])[CH:34]=2)[CH2:30][O:29][C:27]1=[O:28].B(F)(F)F.CCOCC.C([O-])(O)=O.[Na+]>ClCCl>[CH3:42][O:41][C:35]1[CH:34]=[C:33]2[CH2:32][C@H:31]3[CH2:30][O:29][C:27](=[O:28])[C@@H:26]3[CH2:25][C:24]3[C:23]([O:22][CH3:21])=[C:46]([O:47][CH3:48])[C:45]([O:49][CH3:50])=[CH:44][C:43]=3[C:38]2=[CH:37][C:36]=1[O:39][CH3:40]

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 8000Boron trifluoride etherateHCID 9845Trifluoroacetic anhydrideHCID 516892Sodium BicarbonateHCID 14181615HCID 14181615, compound

Product 1

HCID 4429186,7,10,11,12-Pentamethoxy-3a,4,13,13a-tetrahydrodibenzo[4,5:6,7]cycloocta[1,2-c]furan-1(3H)-oneYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

192 mg (1.44 mmole) of hydrated ruthenium oxide (soluble form) suspended in 12 ml of dichloromethane are placed in a 100 ml three-necked flask equipped with a magnetic stirrer, which is swept with argon. 1.5 ml (19 mmoles) of trifluoro acetic acid and 0.8 ml (5.7 mmoles) of trifluoro acetic anhydride are added at ambient temperature. 100 mg (0.24 mmole) of 2-(2,3,4-trimethoxybenzyl)-3-(3,4-dimethoxybenzyl)-4-butanolide dissolved in 8 ml of anhydrous dichloromethane, immediately followed by boron trifluoride etherate (0.2 ml, 1.6 mmole) are added, at ambient temperature, to the suspension which is vigorously stirred. After a few minutes, the supernatant of the solution becomes pale yellow in color. The suspension is thus maintained stirred at ambient temperature overnight, at the end of which time, monitoring by thin layer chromatography indicates the presence of a single product, with the complete disappearance of the starting product. The reaction mixture is treated with NaHCO3 and then filtered through filter paper in order to remove the solid products. The organic phase is then decanted and the aqueous phase extracted with ethyl acetate. The organic phases are then combined, dried over MgSO4 and evaporated to give a pale yellow solio which is chromatographically pure. After filtering through silica (dichloromethane), a white solid (m=98 mg, Yield: 98%) is obtained, which is comparable in all respects (chromatography, IR spectroscopy and 1H NMR spectroscopy) to the compound obtained from the plant species Steganotaenia araliacea Hochst (Umbelliferae), by high resolution analytical liquid chromatography of an ethanolic extract.

Workup

  1. customare placed in a 100 ml three-necked flask
  2. customequipped with a magnetic stirrer
  3. additionare added, at ambient temperature, to the suspension which
  4. waitAfter a few minutes
  5. temperatureThe suspension is thus maintained
  6. stirringstirred at ambient temperature overnight, at the end of which time
  7. filtrationfiltered
  8. filtrationthrough filter paper in order
  9. customto remove the solid products
  10. customThe organic phase is then decanted
  11. extractionthe aqueous phase extracted with ethyl acetate
  12. dry with materialdried over MgSO4
  13. customevaporated
  14. customto give a pale yellow solio which
  15. filtrationAfter filtering through silica (dichloromethane)
  16. customa white solid (m=98 mg, Yield: 98%) is obtained
  17. customobtained from the plant species Steganotaenia araliacea Hochst (Umbelliferae), by high resolution analytical liquid chromatography of an ethanolic extract

Sources & evidence

ORD record
ord-778fd662fb994c1babedb374097f11ef
Source dataset
uspto-grants-1989_10
Patent number
US04873349

Reaction notes

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