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

HRID 1462956ノート

反応式

HRID 1462956 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-45eb40cb01374ab890d9215ca8fb9483
出典データセット
uspto-grants-1984_07
特許番号
US04461907

反応ノート

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