Tetrahydrofuran → Flavone

HRID 908914

反応式

HRID 908914 の反応式
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

参加物

6

反応物 3

HCID 8028TetrahydrofuranHCID 11855845HCID 11855845、化合物HCID 178418361HCID 178418361、化合物

生成物 1

HCID 10680Flavone収率 130.9%

試薬・触媒・溶媒 2

HCID 9942167Palladium hydroxide触媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1482937671aa4fbd88831ae38cc282d2
出典データセット
uspto-grants-2011_09
特許番号
US08017649B2

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