Trifluoroacetic acid → 7,8-dihydronaphtho[2,3-c]furan-1,6(3H,5H)-dione

HRID 2173198Notes

Reaction equation

HRID 2173198 reaction equation
[O:1]=[C:2]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][C:12]([O:14]C(C)(C)C)=O)=[CH:10][C:5]=2[CH2:4][O:3]1.[C:19](O)([C:21](F)(F)F)=O.C(Cl)(=O)C(Cl)=O.[Cl-].[Al+3].[Cl-].[Cl-]>CN(C=O)C>[C:2]1(=[O:1])[C:6]2[CH:7]=[C:8]3[C:9](=[CH:10][C:5]=2[CH2:4][O:3]1)[CH2:11][C:12](=[O:14])[CH2:21][CH2:19]3

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 77230657Tert-butyl (1-oxo-1,3-dihydro-2-benzofuran-5-yl)acetate

Product 1

HCID 675173267,8-dihydronaphtho[2,3-c]furan-1,6(3H,5H)-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a flask charged with tert-butyl (1-oxo-1,3-dihydro-2-benzofuran-5-yl)acetate (375 mg, 2.0 mmol) was added TFA (10 mL). The mixture was allowed to sit at RT for half an hour. LC at that point indicated complete cleavage of the tert-butyl group. The volatiles were removed under reduced pressure. The residue was pumped under high vacuum for 15 minutes before DCM (20 mL) was added to the flask, followed by addition of oxalyl chloride (0.22 mL, 2.5 mmol) and a drop of DMF. The mixture was stirred at RT for 1 hour, and then cooled to 0° C. with an ice bath. Aluminum chloride (780 mg, 5.9 mmol) was added into the reaction. After stirring the solution for 10 minutes, ethylene was bubbled through the reaction with a needle. TLC showed consumption of all material within 1 hour. The crude reaction was dumped into ice, and extracted with DCM (100 mL×3). The extractions were combined, washed with brine, dried over sodium sulfate, adsorbed onto silica gel, and purified by MPLC. The solvent was removed under reduced pressure to afford 7,8-dihydronaphtho[2,3-c]furan-1,6(3H,5H)-dione,

Workup

  1. waitto sit at RT for half an hour
  2. customThe volatiles were removed under reduced pressure
  3. additionwas added to the flask
  4. temperaturecooled to 0° C. with an ice bath
  5. stirringAfter stirring the solution for 10 minutes
  6. customethylene was bubbled through the reaction with a needle
  7. customconsumption of all material within 1 hour
  8. customThe crude reaction
  9. extractionextracted with DCM (100 mL×3)
  10. extractionThe extractions
  11. washwashed with brine
  12. dry with materialdried over sodium sulfate
  13. custompurified by MPLC
  14. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-03326259a68e40d8a77819518215cec6
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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