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

HRID 1728467

반응식

HRID 1728467 반응식
[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]

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 178418476HCID 178418476, 화합물촉매HCID 80711,2-Dimethoxyethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6a293432ee734933a445f4dd54e81c94
출처 데이터셋
uspto-grants-1994_07
특허 번호
US05326900

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