Tetrahydrofuran → HCID 21958334、化合物

HRID 2213702ノート

反応式

HRID 2213702 の反応式
[Mg].C1COCC1.Br[CH2:8][CH:9]1[CH2:14][CH:13]2[CH2:15][CH:10]1[CH:11]=[CH:12]2.Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>CCOCC>[CH2:8]([CH:9]1[CH2:14][CH:13]2[CH2:15][CH:10]1[CH:11]=[CH:12]2)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

参加物

6

反応物 4

HCID 8028Tetrahydrofuran2 回HCID 81401-BromooctaneHCID 27760625-(bromomethyl)bicyclo[2.2.1]hept-2-eneHCID 5462224Magnesium

生成物 1

HCID 21958334HCID 21958334、化合物収率 69.2%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
50 °C

実験手順

An oven-dried 3-neck round bottom flask was charged with magnesium turnings (0.809 g, 0.033 mol) and 40 mL of dry THF. 5-Bromomethyl norbornene (6.001 g, 0.032 mol) was added dropwise at room temperature. The mixture was then heated to 50° C. for 18 hours. In a separate flask, 10 mL of dry THF, Li2CuCl4 (5 mL, 0.0005 mol), and 1-bromooctane (6 mL, 0.035 mol) were combined and placed in a −10° C. ice bath. The Grignard reagent, which was transferred via cannula into an addition funnel, was added dropwise to the cooled solution. After the addition was complete, the solution was warmed to room temperature and stirred for 18 hours. The solution was diluted with ether, washed with NH4Cl, brine, and dried over Na2SO4. The solvent was removed and the product was distilled at 76° C. at 0.4 mbar to yield a clear, colorless liquid (4.88 g, 69%). 1H NMR (300 MHz, CDCl3) δ6.12 (1H endo, dd, J=2.74, 5.49); 6.09–5.99 (2H exo, m); 5.93 (1H endo, dd, J=2.74, 5.49); 2.75 (1H, s); 1.98–1.78 (2H, m); 1.40–1.07 (18H, m); 0.89 (3H, t, J=6.05); 0.52–0.45 (1H, m). 13C NMR (75 MHz, CDCl3) δ137.0; 132.6; 49.7; 45.6; 42.7; 38.9; 35.0; 32.6; 32.1; 30.1; 29.9; 29.8; 29.5; 28.9; 22.9; 14.3.

後処理

  1. customplaced in a −10° C.
  2. additionwas added dropwise to the cooled solution
  3. additionAfter the addition
  4. temperaturethe solution was warmed to room temperature
  5. washwashed with NH4Cl, brine
  6. dry with materialdried over Na2SO4
  7. customThe solvent was removed
  8. distillationthe product was distilled at 76° C. at 0.4 mbar

出典と根拠

ORDレコード
ord-de30ab08c60f437dba1c0896eb1e3a47
出典データセット
uspto-grants-2006_09
特許番号
US07105617B2

反応ノート

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