Methyl 4-(bromomethyl)benzoate → 2-(4-Carbomethoxyphenyl)-1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)ethanone

HRID 1728467

反応式

HRID 1728467 の反応式
[CH3:1][C:2]1([CH3:17])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14](Cl)=[O:15])[CH:5]=[CH:4][C:3]1=2.Br[CH2:19][C:20]1[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][CH:21]=1>C(COC)OC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Zn]>[C:24]([C:23]1[CH:28]=[CH:29][C:20]([CH2:19][C:14]([C:6]2[CH:5]=[CH:4][C:3]3[C:2]([CH3:17])([CH3:1])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]=3[CH:7]=2)=[O:15])=[CH:21][CH:22]=1)([O:26][CH3:27])=[O:25]

参加物

6

反応物 2

HCID 256687Methyl 4-(bromomethyl)benzoateHCID 27954665,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carbonyl chloride

生成物 1

HCID 147264952-(4-Carbomethoxyphenyl)-1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)ethanone

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 178418476HCID 178418476、化合物触媒HCID 80711,2-Dimethoxyethane溶媒2 回

実験手順

A solution of 4 g (16 mmol) of 5,6,7, 8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-carbonyl chloride and 4 g (16 mmol) of methyl 4-bromomethylbenzoate in 20 ml of dimethoxyethane was added dropwise to a solution or suspension of 0.56 g of bis(triphenylphosphine)palladium(II) dichloride and 2.1 g of zinc powder in 40 ml of dimethoxyethane at room temperature. The reaction mixture was then refluxed for 6 h. After cooling, solids were filtered off and the filtrate was heated with active carbon and filtered hot. The filtrate was concentrated and yielded after recrystallization 3x from methanol and finally from isopropanol 0.9 g of the title compound of melting point 103°-104° C.

後処理

  1. temperatureThe reaction mixture was then refluxed for 6 h
  2. temperatureAfter cooling
  3. filtrationsolids were filtered off
  4. temperaturethe filtrate was heated with active carbon
  5. filtrationfiltered hot
  6. concentrationThe filtrate was concentrated
  7. customyielded
  8. customafter recrystallization 3x from methanol

出典と根拠

ORDレコード
ord-6a293432ee734933a445f4dd54e81c94
出典データセット
uspto-grants-1994_07
特許番号
US05326900

関連ノート

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