Hydrochloric Acid → HCID 24742643, compound

HRID 1367603Notes

Reaction equation

HRID 1367603 reaction equation
CC(C)([O-])C.[K+].Br[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([CH2:17][CH2:18][CH3:19])[CH2:14][CH2:15][CH3:16].Cl>O1CCCC1>[CH2:17]([CH:13]([CH2:14][CH2:15][CH3:16])[CH2:12][CH2:11][CH2:10][CH:9]=[CH2:8])[CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 57572811HCID 57572811, compound

Product 1

HCID 24742643HCID 24742643, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a 250 mL flask containing potassium tert-butoxide (13.27 g, 108.7 mmol, 4.6 eq.) under nitrogen atmosphere was added anhydrous tetrahydrofuran (100 mL) and via cannula 1-bromo-6-propylnonane (5.87 g, 23.54 mmol) in solution with anhydrous tetrahydrofuran (20 mL) was transferred at 0° C. The mixture was then stirred at room temperature for 2 h. Hydrochloric acid (230 mL, 1M) was added slowly and the mixture was extracted with cyclohexane (300 mL+3×100 mL). The combined organic phase was washed with aqueous sodium bicarbonate (100 mL, 1M) and dried over magnesium sulfate. The solvent was carefully evaporated under moderate vacuum (at room temperature because of the high volatility of the alkene) to give 3.3 g (84%) of 6-propylnon-1-ene as a brown liquid. 1H NMR (CDCl3, 400 MHz) d?(ppm): 5.82 (ddt, J=6.8 Hz, J=10.2 Hz, J=16.9 Hz, H); 5.00 (broad d, J=16.9 Hz, H); 4.93 (broad d, J=10.2 Hz, H); 2.02 (dt, J=6.8 Hz, J=6.8 Hz, 2H); 1.41-1.30 (m, 2H); 1.32-1.15 (m, 11H); 0.88 (t, J=7.1 Hz, 6H′). 13C NMR (CDCl3, 129.9 MHz) d?(ppm): 139.3; 114.1; 36.8; 36.1 (2C); 34.3; 33.2; 26.0; 19.8 (2C); 14.5 (2C). MS (IE) m/z (%) 169.1 [M+] (25); 141.1 (30); 125.0 (57); 113.0 (40); 99.0 (44); 85.0 (67); 71.0 (73).

Workup

  1. customwas transferred at 0° C
  2. extractionthe mixture was extracted with cyclohexane (300 mL+3×100 mL)
  3. washThe combined organic phase was washed with aqueous sodium bicarbonate (100 mL, 1M)
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was carefully evaporated under moderate vacuum (at room temperature because of the high volatility of the alkene)

Sources & evidence

ORD record
ord-6f01cd69fab84255a9c1161c4280a935
Source dataset
uspto-grants-2011_02
Patent number
US07893258B2

Reaction notes

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