Imidazole → 6-Chloro-2,3-dihydro-7-hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

HRID 1724615ノート

反応式

HRID 1724615 の反応式
N1C=CN=C1.[Cl:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[O:17]C(=O)C)[O:13][CH2:12][CH:11]([C:21]1[CH:26]=[CH:25][C:24]([O:27]C(=O)C)=[CH:23][CH:22]=1)[C:10]2=[O:31]>C(O)C>[Cl:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[OH:17])[O:13][CH2:12][CH:11]([C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1)[C:10]2=[O:31]

参加物

4

反応物 2

HCID 795ImidazoleHCID 9842545HCID 9842545、化合物

生成物 1

HCID 99260276-Chloro-2,3-dihydro-7-hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one収率 802.7%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Imidazole (0.60 g) was added to a suspension of 6-chloro-4′,7-diacetoxyisoflavan-4-one (0.24 g, 0.06 mmol) in absolute ethanol (5.0 ml) and the mixture was refluxed for 45 min under argon. The solution was concentrated under reduced pressure and distilled water (10 ml) was added to the residue. The mixture was left overnight in the fridge and the resulting precipitate was filtered, washed with water and dried to yield 6-chloro-4′,7-dihydroxyisoflavan-4-one (0.14 g, 75%) as a white powder. 1H NMR (d6-acetone): δ 3.87 (t, 1H, J 7.2 Hz, H3), 4.64 (d, 2H, J 6.2 Hz, H2), 6.59 (s, 1H, H8), 6.78 (d, 2H, J 8.7 Hz, ArH), 7.10 (d, 2H, J 8.7 Hz, ArH), 7.70 (bs, 1H, OH), 7.77 (s, 1H, H5).

後処理

  1. temperaturethe mixture was refluxed for 45 min under argon
  2. concentrationThe solution was concentrated under reduced pressure
  3. distillationdistilled water (10 ml)
  4. additionwas added to the residue
  5. filtrationthe resulting precipitate was filtered
  6. washwashed with water
  7. customdried

出典と根拠

ORDレコード
ord-c65eb4a3aa1e43cfa4d65f4bf0d2aef4
出典データセット
uspto-grants-2009_02
特許番号
US07488494B2

反応ノート

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