1,1-Dibromoethane → 3-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propyne

HRID 428222

反応式

HRID 428222 の反応式
[Mg].BrC(Br)C.Br[C:7]1[CH:16]=[CH:15][C:14]2[C:13]([CH3:18])([CH3:17])[CH2:12][CH2:11][C:10]([CH3:20])([CH3:19])[C:9]=2[CH:8]=1.CO[CH:23]=[C:24]=[CH2:25].[Cl-].[NH4+]>C1COCC1>[CH3:17][C:13]1([CH3:18])[CH2:12][CH2:11][C:10]([CH3:20])([CH3:19])[C:9]2[CH:8]=[C:7]([CH2:25][C:24]#[CH:23])[CH:16]=[CH:15][C:14]1=2

参加物

7

反応物 5

HCID 112011,1-DibromoethaneHCID 25517Ammonium ChlorideHCID 1394031-Methoxypropa-1,2-dieneHCID 2266856-Bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthaleneHCID 5462224Magnesium

生成物 1

HCID 177738693-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-1-propyne収率 47%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
50 °C

実験手順

20 g (0.82 mol) of magnesium activated with 0.1 ml of dibromoethane are introduced into a four litre reactor under a stream of nitrogen. A solution of 200 g (0.75 mol) of 2-bromo-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene is added dropwise so as to maintain the reflux of the THF and the mixture is stirred at 50° C. for two hours. The reaction medium is then cooled to −5° C. and 1.2 g (8.2 mmol) of CuBr are added and a solution of 58 g (0.82 mol) of methoxyallene in 100 ml of THF is introduced dropwise. The mixture is stirred for one hour at −5° C. and is then allowed to return to room temperature and is stirred for two hours. The reaction medium is poured into saturated ammonium chloride solution and extracted with ethyl acetate, and the organic phase is separated out after settling has taken place, dried over magnesium sulphate and evaporated. The oil obtained is distilled at 0.02 mm Hg and the fraction passing at 95-100° C. is collected. 79 g (47%) of the expected product are obtained in the form of a colourless oil.

後処理

  1. additionare introduced into a four litre reactor under a stream of nitrogen
  2. temperatureto maintain the
  3. temperatureThe reaction medium is then cooled to −5° C.
  4. stirringThe mixture is stirred for one hour at −5° C.
  5. customto return to room temperature
  6. stirringis stirred for two hours
  7. extractionextracted with ethyl acetate
  8. customthe organic phase is separated out after settling
  9. dry with materialdried over magnesium sulphate
  10. customevaporated
  11. customThe oil obtained
  12. distillationis distilled at 0.02 mm Hg
  13. custompassing at 95-100° C.
  14. customis collected

出典と根拠

ORDレコード
ord-6c3aed9c74eb4c98968b6f85f068140e
出典データセット
uspto-grants-2001_11
特許番号
US06313162B1

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