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

HRID 1891430ノート

反応式

HRID 1891430 の反応式
[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

参加物

4

反応物 1

HCID 219100Phenoxodiol

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

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).

後処理

  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%)

出典と根拠

ORDレコード
ord-d7af4d2e59c34c2e8d272914aeb30b76
出典データセット
uspto-grants-2013_08
特許番号
US08507549B2

反応ノート

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