Tetrahydrofuran → Flavone

HRID 908914

Reaction equation

HRID 908914 reaction equation
C(OC(CCCCC(O[C:18]1[C:27](=[O:28])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[O:20][C:19]=1[C:29]1[CH:34]=[CH:33][C:32](OC(CCCCC(OCC2C=CC=CC=2)=O)=O)=[CH:31][CH:30]=1)=O)=O)C1C=CC=CC=1.[H][H].C1COCC1>CCOC(C)=O.[OH-].[OH-].[Pd+2]>[O:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:27](=[O:28])[CH:18]=[C:19]1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 11855845HCID 11855845, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10680FlavoneYield 130.9%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3,4′-di-(benzyloxycarbonylbutylcarbonyloxy)flavone (435 mg, 0.629 mmol) and Pd(OH)2 (50 mg) in EtOAc (5 mL) was treated with hydrogen for 2 h resulting in a grey precipitate. THF was added to dissolve the precipitate and the mixture was filtered (Celite). The pad washed with THF, and the filtrate concentrated. The solid residue was recrystallised from THF/petrol to afford the bis(hemiadipate) as a colourless solid (183 mg, 50%); mp 133° C.; 1H NMR (500 MHz, d6-DMSO) δ 1.55-1.70 (m, 8H, CH2CH2), 2.24 (t, 2H, J=7.0 Hz, CH2CO), 2.27 (t, 2H, J=7.0 Hz, CH2CO), 2.63 (t, 2H, J=7.0 Hz, CH2CO), 2.64 (t, 2H, J=7.0 Hz, CH2CO), 7.37 app. d, 2H, J=9.0 Hz, H3′,5′), 7.55 (dd, 1H, J5,6=8.5, J6,7=7.5, Hz, H6), 7.80 (d, 1H, J7,8=8.5 Hz, H8), 7.88 (ddd, 1H, J6,7=7.5, J7,8=8.5, J5,7=1.5 Hz, H7), 7.96 (app. d, 2H, J=9.0 Hz, H2′,6′), 8.08 (dd, 1H, J5,6=8.5, J5,7=1.5 Hz, H5); 13C NMR (125 MHz, d6-DMS) δ 23.77, 23.82, 32.6, 33.2, 33.3; 44.3 (CH2), 118.7, 122.5, 122.6, 122.7, 125.1, 126.8, 129.7, 132.9, 134.8, 152.7, 154.9, 155.1 (Ar), 170.4, 171.1, 171.4, 174.3, 174.3 (5C, C═O); IR 3059, 2940, 2873, 1768, 1706, 1504, 759 cm−1; HRMS (ESI−) m/z 509.1441, C27H25O10 [M−H]− requires 509.1442.

Workup

  1. customresulting in a grey precipitate
  2. dissolutionto dissolve the precipitate
  3. filtrationthe mixture was filtered (Celite)
  4. washThe pad washed with THF
  5. concentrationthe filtrate concentrated
  6. customThe solid residue was recrystallised from THF/petrol

Sources & evidence

ORD record
ord-1482937671aa4fbd88831ae38cc282d2
Source dataset
uspto-grants-2011_09
Patent number
US08017649B2

Linked notes

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