Imidazole → 3(2H)-Isoflavene

HRID 603280노트

반응식

HRID 603280 반응식
N1C=CN=C1.C(O[C:10]1[CH:19]=[C:18]2[C:13]([CH:14]=[C:15]([C:20]3[CH:25]=[CH:24][C:23](OC)=[CH:22][CH:21]=3)[CH2:16][O:17]2)=[CH:12][CH:11]=1)(=O)C>C(O)C>[O:17]1[C:18]2[C:13](=[CH:12][CH:11]=[CH:10][CH:19]=2)[CH:14]=[C:15]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:16]1

참가 물질

4

반응물 2

HCID 795ImidazoleHCID 264550MLS002703491

생성물 1

HCID 5004603(2H)-Isoflavene

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

Imidazole (0.18 g) was added to a suspension of 7-acetoxy-4′-methoxyisoflav-3-ene (0.06 g, 0.02 mmol) in absolute ethanol (5.0 ml) and the mixture was refluxed for 45 minutes under argon. The solution was concentrated under reduced pressure and the product was precipitated by addition of distilled water (10 ml). The mixture was left overnight in the fridge and filtered to yield isoflav-3-ene. The crude product was recrystallised from methanol/benzene to yield 7-hydroxy-4′-methoxyisoflav-3-ene (0.034 g, 66%). 1H NMR (CDCl3+d6-DMSO): δ 3.74 (s, 3H, OCH3), 4.99 (s, 2H, H2), 6.21 (d, 1H, J 2.3 Hz, H8), 6.29 (dd, 1H, J 2.3 Hz, 8.3 Hz, H6), 6.67 (bs, 1H, H4), 6.85 (d, 1H, J 8.3 Hz, H5), 6.86 (d, 2H, J 8.7 Hz, ArH), 7.33 (d, 2H, J 8.7 Hz, ArH).

후처리

  1. temperaturethe mixture was refluxed for 45 minutes under argon
  2. concentrationThe solution was concentrated under reduced pressure
  3. customthe product was precipitated by addition of distilled water (10 ml)
  4. filtrationfiltered

출처 및 근거

ORD 기록
ord-107dd5d8e21a43ffad44953eab33cd2c
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906660B2

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