Tetrahydrofuran → Flavonol

HRID 908911

반응식

HRID 908911 반응식
C(OC(CCCCC([O:17][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][CH:32]=[CH:31][CH:30]=1)=O)=O)C1C=CC=CC=1.C1COCC1>[OH-].[OH-].[Pd+2].CCO>[OH:17][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:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

참가 물질

5

반응물 2

HCID 8028TetrahydrofuranHCID 118553053-(Benzyloxycarbonylbutylcarbonyloxy)flavone

생성물 1

HCID 11349Flavonol수율 126.5%

시약·촉매·용매 2

HCID 9942167Palladium hydroxide촉매HCID 702Ethanol용매

실험 절차

A mixture of 3-(benzyloxycarbonylbutylcarbonyloxy)flavone (312 mg, 0.7 mmol) and Pd(OH)2 (49.4 mg) in 9:1 THF:EtOH+0.05% acetic acid (15 mL) was treated with H2 for 5 h. The crude product was filtered (Celite), the filtrate was concentrated and the residue was purified by flash chromatography (10-25% EtOAc in toluene+1% acetic acid) to give the hemiadipate as a light yellow solid (0.211 g, 89%). A small portion was crystallized from EtOAc/petroleum spirits, mp=118-121° C.; 1H NMR (399.7 MHz, CDCl3) δ 1.66-1.83 (m, 4H, CH2CH2CO2); 2.38 (t, J=6.8 Hz, 2H, CH2CO2); 2.63 (t, J=6.8 Hz, 2H, CH2CO2); 7.42 (dd, 1H, J5,6=8.0 Hz, J6,7=8.0 Hz, H6); 7.47-7.53 (m, 3H, H3′,4′, 5′); 7.54 (d, 1H, J7,8=8.4 Hz, H8); 7.70 (ddd, 1H, J5,7=1.6 Hz, J6,7=8.0 Hz, J7,8=8.4 Hz, H7); 7.81-7.86 (m, 2H, H2′, 6′); 8.24 (dd, 1H, J5,6=8.0 Hz, J5,7=1.6 Hz, H5). 13C NMR (100.5 MHz, CDCl3) δ 25.01, 25.20 (2C, CO2CH2CH2); 34.57 (2C, CO2CH2); 119.20, 124.66, 126.33, 127.21, 129.41, 129.76, 131.04, 132.40, 134.70, 135.10, 156.74, 157.60 (14C, Ar); 171.52, 173.38, 179.36 (3C, C═O). Anal. Found: C, 68.89; H, 4.91; C21H18O6 requires C, 68.85; H, 4.95%. HRMS (ESI+) m/z 389.1000, C21H18NaO6 [M+Na]+ requires 389.1001].

후처리

  1. filtrationThe crude product was filtered (Celite)
  2. concentrationthe filtrate was concentrated
  3. customthe residue was purified by flash chromatography (10-25% EtOAc in toluene+1% acetic acid)

출처 및 근거

ORD 기록
ord-b23d0159589d48b1b0d1c2cda6cfd22b
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08017649B2

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