Triethylamine → 7-Methyl-9-(3-(phenyl)propoxy)-5H-furo[3,2-g]chromen-5-one

HRID 1875366Notes

Reaction equation

HRID 1875366 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][O:10][C:11]2[C:12]3[O:32][CH:31]=[CH:30][C:13]=3[C:14](S(C(F)(F)F)(=O)=O)=[C:15]3[C:20]=2[O:19][C:18]([CH3:21])=[CH:17][C:16]3=[O:22])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])=O.C([NH+](CC)CC)C.C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C)C=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:21][C:18]1[O:19][C:20]2[C:15]([C:16](=[O:22])[CH:17]=1)=[CH:14][C:13]1[CH:30]=[CH:31][O:32][C:12]=1[C:11]=2[O:10][CH2:9][CH2:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 10219518Triethylazanium;formateHCID 687138709-(3-Phenylpropoxy)-7-methyl-4-trifluoromethanesulfonyl-5H-furo[3,2-g]chromen-5-one

Product 1

HCID 592724047-Methyl-9-(3-(phenyl)propoxy)-5H-furo[3,2-g]chromen-5-oneYield 75%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

9-(3-Phenylpropoxy)-7-methyl-4-trifluoromethanesulfonyl-5H-furo[3,2-g]chromen-5-one (1.5 g, 3.11 mmol, 0.2M, prepared from the corresponding 4-hydroxy system according to General Procedure G, Step 1) was dissolved in anhydrous dimethylformamide and treated with triethylammonium formate (1.8 g, 12.4 mmol.). The reaction flask was evacuated and back-filled with N2 three times. Anhydrous triethylamine (0.63 g, 6.20 mmol), Pd(OAc)2 (70 mg, 0.31 mmol) and triphenylphosphine (0.16 mg, 0.62 mmol) were added to the reaction mixture and the flask was again evacuated and back-filled with N2. The reaction mixture was heated to 60-70° C. for 24 hours under a N2 atmosphere. The solvents were removed under vacuum and the residue was dissolved in ethyl acetate and washed with saturated aqueous NH4Cl solution. The organic layer was dried over MgSO4, concentrated under vacuum and the crude residue was purified by silica gel chromatography, eluting with diethyl ether:dichloromethane (0:1, then 1:3) to afford the title compound as a pale yellow solid (75%). 1H NMR (300 MHz, CDCl3) δ: 2.06-2.16 (m, 2H), 2.41 (s, 3H, CH3), 2.92 (t, J=7.5 Hz, 2H), 4.49 (t, J=6.6 Hz, 2H), 6.15 (s, 1H), 6.85 (d, J=2.1 Hz, 1H), 7.16-7.30 (m, 5H), 7.69 (d, J=2.1 Hz, 1H), 8.09 (s, 1H). MS (ES+) m/z: 335 (M+H+).

Workup

  1. customThe reaction flask was evacuated
  2. additionback-filled with N2 three times
  3. customthe flask was again evacuated
  4. additionback-filled with N2
  5. customThe solvents were removed under vacuum
  6. dissolutionthe residue was dissolved in ethyl acetate
  7. washwashed with saturated aqueous NH4Cl solution
  8. dry with materialThe organic layer was dried over MgSO4
  9. concentrationconcentrated under vacuum
  10. customthe crude residue was purified by silica gel chromatography
  11. washeluting with diethyl ether:dichloromethane (0:1

Sources & evidence

ORD record
ord-0785b02493874abfaad3a89a75e223d7
Source dataset
uspto-grants-2012_11
Patent number
US08309545B2

Reaction notes

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