1-(5-Chloro-2-hydroxyphenyl)-3-(4-chlorophenyl)prop-2-en-1-one → 6-Chloro-2-(4-chlorophenyl)-2H-1-benzopyran

HRID 1462956노트

반응식

HRID 1462956 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]([C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=2[OH:19])=O)=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH:9]=[CH:10][C:12]3[C:13](=[CH:14][CH:15]=[C:16]([Cl:18])[CH:17]=3)[O:19]2)=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 978941-(5-Chloro-2-hydroxyphenyl)-3-(4-chlorophenyl)prop-2-en-1-oneHCID 4311764Sodium borohydride

생성물 1

HCID 162052936-Chloro-2-(4-chlorophenyl)-2H-1-benzopyran수율 55.5%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

4,5'-Dichloro-2'-hydroxychalcone (7.32 g) was dissolved in ethanol (100 ml) and sodium borohydride (1.89 g) added in small portions. The reaction mixture was stirred for 1 hr at room temperature, evaporated to dryness, and diluted with water. The precipitated solid was filtered off, washed with water, and heated with acetic acid (100 ml) on the steam bath for 2 hr. The acetic acid was evaporated the residue dissolved in dichloromethane, and the solution washed sequentially with water, saturated sodium bicarbonate solution, and water, dried and evaporated. The residue was chromatographed on alumina, eluting with toluene, to give 4',6-dichloroflav-3-ene (3.84 g) as a colourless oil, identified by n.m.r. spectroscopy.

후처리

  1. customevaporated to dryness
  2. additiondiluted with water
  3. filtrationThe precipitated solid was filtered off
  4. washwashed with water
  5. temperatureheated with acetic acid (100 ml) on the steam bath for 2 hr
  6. customThe acetic acid was evaporated the residue
  7. dissolutiondissolved in dichloromethane
  8. washthe solution washed sequentially with water, saturated sodium bicarbonate solution, and water
  9. customdried
  10. customevaporated
  11. customThe residue was chromatographed on alumina
  12. washeluting with toluene

출처 및 근거

ORD 기록
ord-45eb40cb01374ab890d9215ca8fb9483
출처 데이터셋
uspto-grants-1984_07
특허 번호
US04461907

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