1,2-Dibromoethane → Ethyl 2-[5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl]benzoate

HRID 428231

반응식

HRID 428231 반응식
[Mg].Br[C:3]1[CH:12]=[CH:11][C:10]2[C:9]([CH3:14])([CH3:13])[CH2:8][CH2:7][C:6]([CH3:16])([CH3:15])[C:5]=2[CH:4]=1.BrCCBr.[CH2:21]([O:23][C:24](=[O:32])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1Br)[CH3:22]>C1COCC1.C(OCC)C.C(OC(=O)C)C.[Cl-].[Cl-].[Zn+2]>[CH3:13][C:9]1([CH3:14])[CH2:8][CH2:7][C:6]([CH3:16])([CH3:15])[C:5]2[CH:4]=[C:3]([C:30]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:24]([O:23][CH2:21][CH3:22])=[O:32])[CH:12]=[CH:11][C:10]1=2

참가 물질

8

반응물 4

HCID 78391,2-DibromoethaneHCID 80186Ethyl 2-bromobenzoateHCID 2266856-Bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene2회HCID 5462224Magnesium

생성물 1

HCID 18357939Ethyl 2-[5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl]benzoate

시약·촉매·용매 3

HCID 3007855Zincchloride촉매HCID 8028Tetrahydrofuran용매4회HCID 21584169Diethylether ethylacetate용매

실험 절차

To magnesium (180 mgs, 7.5 mmols) in THF (3 ml) was added a solution of 2-bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene (200 mgs) in THF (5 ml) followed by 1,2-dibromoethane (94 mgs, 0.5 mmol). The mixture was stirred for 15 mins, then another portion of 2-bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene (1.14 g, 5 mmols) in THF (10 ml) was added. The mixture was stirred for 15 mins at room temperature, and refluxed for 1 h. ZnCl2 (680 mgs, 5 mmols) was added, stirred for 40 mins, and to the white precipitate. ethyl-2-bromobenzoate (1.09 g) in THF (5 ml) was added, immediately followed by addition of Ni(PPh2CH2CH2)Cl2 (26 mgs, 0.05 mmols). The mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with diethyl ether:ethylacetate (1:1, a total of 180 ml), the organic phase was washed with water (10 ml), brine (10 ml) NaHCO3 (10 ml) and brine (10 ml), dried (MgSO4) and the solvent was removed under reduced pressure. Silicagel chromatography (5% ethyl acetate in hexane) followed by HPLC purification of the crude material gave the title compound as a colorless oil.

후처리

  1. stirringThe mixture was stirred for 15 mins at room temperature
  2. temperaturerefluxed for 1 h
  3. stirringstirred for 40 mins
  4. stirringThe mixture was stirred at room temperature for 16 h
  5. washa total of 180 ml), the organic phase was washed with water (10 ml), brine (10 ml) NaHCO3 (10 ml) and brine (10 ml)
  6. dry with materialdried (MgSO4)
  7. customthe solvent was removed under reduced pressure
  8. customSilicagel chromatography (5% ethyl acetate in hexane) followed by HPLC purification of the crude material

출처 및 근거

ORD 기록
ord-85504433ac2b43f3b0cf4090e0563cc0
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313163B1

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