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

HRID 428231

反応式

HRID 428231 の反応式
[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

参加物

8

反応物 4

HCID 78391,2-DibromoethaneHCID 80186Ethyl 2-bromobenzoateHCID 2266856-Bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene2 回HCID 5462224Magnesium

生成物 1

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

試薬・触媒・溶媒 3

HCID 3007855Zincchloride触媒HCID 8028Tetrahydrofuran溶媒4 回HCID 21584169Diethylether ethylacetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-85504433ac2b43f3b0cf4090e0563cc0
出典データセット
uspto-grants-2001_11
特許番号
US06313163B1

関連ノート

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