Trifluoroacetic acid → 6-(hydroxymethyl)-1,6,7,8-tetrahydro-3H-indeno[4,5-c]furan-3-one

HRID 1187042Notes

Reaction equation

HRID 1187042 reaction equation
[CH:1]1([CH2:12][OH:13])[C:9]2[C:4](=[C:5]([CH2:10][OH:11])[CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.FC(F)(F)[C:16]([O-])=[O:17].[Tl+].C(O)(C(F)(F)F)=O.[Cl-].[Li+].[O-2].[Mg+2]>[Pd](Cl)Cl.CCOC(C)=O.C(Cl)Cl.CO>[OH:13][CH2:12][CH:1]1[C:9]2[CH:8]=[CH:7][C:6]3[C:16](=[O:17])[O:11][CH2:10][C:5]=3[C:4]=2[CH2:3][CH2:2]1

Participants

10

Reactant 5

HCID 6422Trifluoroacetic acidHCID 433294Lithium ChlorideHCID 6850729Magnesium monoxideHCID 21902506Thallium(1+);2,2,2-trifluoroacetateHCID 666465392,3-dihydro-1H-indene-1,4-diyldimethanol

Product 1

HCID 684332706-(hydroxymethyl)-1,6,7,8-tetrahydro-3H-indeno[4,5-c]furan-3-one

Reagents, catalysts & solvents 4

HCID 24290Palladium ChlorideCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a flask charged with 2,3-dihydro-1H-indene-1,4-diyldimethanol (210 mg, 1.2 mmol) and a stir bar was added thallium trifluoroacetate (770 mg, 1.4 mmol) and TFA (2 mL) at 0° C. The mixture was allowed to stir for 16 hours. LC showed no SM left at that point. The volatiles were removed under reduced pressure, and the residue was dissolved in DCM and concentrated twice to affect azeotropic removal of all TFA. After pumping the residue under high vacuum for 20 minutes, palladium chloride (21 mg, 0.18 mmol), lithium chloride (75 mg, 1.8 mmol), magnesium oxide (190 mg, 4.7 mmol), and MeOH (10 mL) were added to the flask. The mixture was treated under an atmosphere of CO for 2 hours. To this mixture was added DCM and EtOAc to precipitate all the inorganic solids. The crude solution was filtered through a celite pad, and the filtrate was collected, adsorbed onto silica gel, and purified by MPLC to afford 6-(hydroxymethyl)-1,6,7,8-tetrahydro-3H-indeno[4,5-c]furan-3-one.

Workup

  1. waitleft at that point
  2. customThe volatiles were removed under reduced pressure
  3. dissolutionthe residue was dissolved in DCM
  4. concentrationconcentrated twice
  5. customremoval of all TFA
  6. customfor 20 minutes
  7. additionThe mixture was treated under an atmosphere of CO for 2 hours
  8. customto precipitate all the inorganic solids
  9. filtrationThe crude solution was filtered through a celite pad
  10. customthe filtrate was collected
  11. custompurified by MPLC

Sources & evidence

ORD record
ord-02aaf16c729b42938591f11fb25016dc
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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