Phenoxodiol → 4',7-Dihydroxy-3,4-dihydroisoflavone

HRID 1891430노트

반응식

HRID 1891430 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][O:10][C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[C:13]([OH:18])[CH:12]=3)=[CH:4][CH:3]=1>CO.[Pd]>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:17][C:16]3[C:11](=[CH:12][C:13]([OH:18])=[CH:14][CH:15]=3)[O:10][CH2:9]2)=[CH:4][CH:3]=1

참가 물질

4

반응물 1

HCID 219100Phenoxodiol

생성물 1

HCID 3829754',7-Dihydroxy-3,4-dihydroisoflavone

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

To a solution of 3-(4-hydroxy-phenyl)-2H-chromen-7-ol (P7) (0.241 g, 1 mmol) in MeOH was added 10% Pd—C (0.050 g). This reaction mixture was hydrogenated at room temperature under 2 atm (30 psi) of H2 pressure for ca. 6 hours. After the disappearance of starting material (TLC), the catalyst was filtered through a pad of celite. The celite-pad was washed with 10 mL of THF then 2×10 mL of MeOH. The solution was filtered once more through filter paper and evaporated to obtain the brownish solid residue which was chromatographed over silica gel using CH2Cl2:MeOH (6:1) to get (0.169 g, 70%) reddish white solid P8. 1H NMR (600 MHz, Acetone-d6) δ,7.08 (d, 2H, J=8.4 Hz, Ar—H2′/H6′), 6.82 (d, 1H, J=7.8 Hz, Ar—H5), 6.80 (d, 2H, J=8.4 Hz, Ar—H3′/H5′), 6.35, (dd, 1H, 2J=7.8 Hz, 3J=2.4 Hz), 6.27 (d, 1H, 3J=2.4 Hz), 4.15 (m, 1H, O—CH), 3.88 (t, 1H, J=10.8 Hz, O—CH), 3.0 (m, 1H, 3-CH), 2.9 (m, 2 H, 4-CH2).

후처리

  1. filtrationAfter the disappearance of starting material (TLC), the catalyst was filtered through a pad of celite
  2. washThe celite-pad was washed with 10 mL of THF
  3. filtrationThe solution was filtered once more
  4. filtrationthrough filter paper
  5. customevaporated
  6. customto obtain the brownish solid residue which
  7. customwas chromatographed over silica gel
  8. customto get (0.169 g, 70%)

출처 및 근거

ORD 기록
ord-d7af4d2e59c34c2e8d272914aeb30b76
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507549B2

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