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

HRID 1724615노트

반응식

HRID 1724615 반응식
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]

참가 물질

4

반응물 2

HCID 795ImidazoleHCID 9842545HCID 9842545, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c65eb4a3aa1e43cfa4d65f4bf0d2aef4
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07488494B2

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