HCID 11855570, compound → 2H-1-BENZOPYRAN-2-ONE, 2-(4-HYDROXYPHENYL)-

HRID 908912Notes

Reaction equation

HRID 908912 reaction equation
C([O:8][C:9]1[CH:42]=[CH:41][C:12]([C:13]2[O:14][C:15]3[C:20]([C:21](=[O:40])[C:22]=2OC(CCCCC(OCC2C=CC=CC=2)=O)=O)=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:11][CH:10]=1)C1C=CC=CC=1.[H][H]>C1COCC1.C(O)C.CC(O)=O.[OH-].[OH-].[Pd+2]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]2[O:14][C:15]3[C:20]([C:21](=[O:40])[CH:22]=2)=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:41][CH:42]=1

Participants

7

Reactant 2

HCID 11855570HCID 11855570, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 2290162H-1-BENZOPYRAN-2-ONE, 2-(4-HYDROXYPHENYL)-Yield 88.6%

Reagents, catalysts & solvents 4

HCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the 4′-(benzyloxy)-3-(benzyloxycarbonyl butylcarbonyloxy) flavone (400 mg, 0.711 mmol) and Pd(OH)2 (56 mg) in THF (10 mL), ethanol (1.2 mL) and AcOH (100 μL) was treated with hydrogen (50 psi) for 18 h. The reaction mixture was then filtered (Celite) and the pad washed with THF. The filtrate was concentrated and the solid residue was purified by flash chromatography (70% THF/toluene+1% AcOH) and the resultant solid recrystallised from THF/petrol to afford the acid as a colourless solid (150 mg, 55%); mp 177-180° C.; 1H NMR (500 MHz, d6-DMSO) δ 1.56-1.66 (m, 4H, CH2CH2), 2.25 (t, 2H, J=7.0 Hz, CH2CO), 2.64 (t, 2H, J=7.0 Hz, CH2CO), 6.96 (app. d, 2H, J=8.5 Hz, H2′,6′), 7.52 (t, 1H, J6,7=J7,8=7.5 Hz, H7), 7.80 (app. d, 2H, J=7.5 Hz, H3′,5′), 7.78 (m, 1H, H8), 7.85 (t, 1H, J5,6=J6,7=7.5 Hz, H6), 8.06 (d, 1H, J5,6=8.0 Hz, H5); 13C NMR (125 MHz, d6-DMSO) δ 23.8, 23.9, 32.9, 33.3 (4C, CH2), 115.9, 118.5, 119.7, 122.7, 125.0, 125.6, 130.1, 131.9, 134.5, 154.9, 155.8 160.6 (Ar), 170.4 170.9, 174.3 (3C, C═O); IR 3257, 2944, 2869, 1765, 1706, 1595, 854 cm−1; HRMS (ESI+) m/z 383.1123, C21H19O7 [M+H]+ requires 383.1131.

Workup

  1. filtrationThe reaction mixture was then filtered (Celite)
  2. washthe pad washed with THF
  3. concentrationThe filtrate was concentrated
  4. customthe solid residue was purified by flash chromatography (70% THF/toluene+1% AcOH)
  5. customthe resultant solid recrystallised from THF/petrol

Sources & evidence

ORD record
ord-de67402462cf4ddcbfecaa314b1c9871
Source dataset
uspto-grants-2011_09
Patent number
US08017649B2

Reaction notes

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