Tetrahydrofuran → HCID 21958334, compound

HRID 2213702Notes

Reaction equation

HRID 2213702 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

HCID 21958334HCID 21958334, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
50 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-de30ab08c60f437dba1c0896eb1e3a47
Source dataset
uspto-grants-2006_09
Patent number
US07105617B2

Reaction notes

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