Iodobenzene → 5-phenoxy-3,4-dihydronaphthalen-1(2H)-one

HRID 63080

反応式

HRID 63080 の反応式
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C:7]2=[O:12].I[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[H-].[Na+].COCCOCCN(CCOCCOC)CCOCCOC>CN(C=O)C.O.Cl[Cu]>[O:1]([C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C:7]2=[O:12])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

参加物

8

反応物 4

HCID 11575IodobenzeneHCID 24758Sodium hydrideHCID 112414Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-HCID 1199215-Hydroxy-1-tetralone

生成物 1

HCID 107286255-phenoxy-3,4-dihydronaphthalen-1(2H)-one収率 18%

試薬・触媒・溶媒 3

HCID 62652Cuprous chloride触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

To a solution of 5-hydroxy-1-tetralone (4.5 g, 28.0 mmol) and iodobenzene (24.0 g, 168.0 mmol) in DMF (50 mL) was added NaH (1.2 g, 30.0 mmol) at room temperature. The mixture was heated to 50° C. until the solid was dissolved and then cooled. To the mixture was added CuCl (2.8 g, 28.0 mmol); followed by tris(dioxa 3,6-heptyl)amine (2.7 g, 8.4 mmol). The mixture was heated at 145° C. overnight. The reaction was diluted with water, extracted with EtOAc, washed with brine, dried (Na2SO4), and concentrated. Purification by silica gel chromatography (20:1 PE/EtOAc) gave 1.2 g (18%) of the title compound as a yellow oil. [M+H] calc'd for C16H14O2, 239; found 239.

後処理

  1. dissolutionwas dissolved
  2. temperaturecooled
  3. temperatureThe mixture was heated at 145° C. overnight
  4. extractionextracted with EtOAc
  5. washwashed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customPurification by silica gel chromatography (20:1 PE/EtOAc)

出典と根拠

ORDレコード
ord-328b236c2f914b0ca6c088a7a6bd926a
出典データセット
uspto-grants-2016_09
特許番号
US09447045B2

関連ノート

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