4-Bromo-2-methylbut-1-ene → HCID 117664395, compound

HRID 2199486Notes

Reaction equation

HRID 2199486 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[C:8](/[CH:14]=[CH:15]/[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Na].[CH2:23](Br)[CH2:24][C:25]([CH3:27])=[CH2:26]>CCOCC>[OH:1][C:2]1[C:11]([CH2:23][CH2:24][C:25]([CH3:27])=[CH2:26])=[C:10]([O:12][CH3:13])[CH:9]=[C:8](/[CH:14]=[CH:15]/[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 5495854-Bromo-2-methylbut-1-eneHCID 5360545SodiumHCID 71626584HCID 71626584, compound

Product 1

HCID 117664395HCID 117664395, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Dissolve compound 7 (5 g, 0.0176 mol) in 50 ml ether, add sodium metal (0.43 g, 0.0184 mol) into the solution, stir at room temperature for 4 h, then add in isopentenyl bromide (3.2 g, 0.0211 mol), reflux to react for 4 h, stop the reaction. Wash the reaction solution successively with water and saturated brine, separate the organic layer. Desiccate the organic layer over anhydrous magnesium sulfate, filter the solution and remove the solvent by rotary evaporation to obtain a yellow oil which is then feeded to silica gel column chromatography and evaporate the solvent in the eluent to obtain 3.8 g white solid (61%). 1H-NMR (400M, CDCl3) δ (ppm): 1.61 (s, 3H), 1.71 (s, 3H), 34 (d, J=6.8 Hz, 2H), 3.91 (s, 3H), 3.94 (s, 3H), 5.12 (t, J=6.8 Hz, 1H), 6.78 (s, 1H), 7.00 (d, J=16 Hz, 1H), 7.27 (t, J=7.2 Hz, 1H), 7.38 (t, J=7.2 Hz, 2H), 7.52 (d, J=7.2 Hz, 2H), 7.84 (d, J=16 Hz, 1H), 11.66 (s, 1H).

Workup

  1. temperaturereflux
  2. customto react for 4 h
  3. customthe reaction
  4. washWash the reaction solution successively with water and saturated brine
  5. customseparate the organic layer
  6. filtrationDesiccate the organic layer over anhydrous magnesium sulfate, filter the solution
  7. customremove the solvent
  8. customby rotary evaporation
  9. customto obtain a yellow oil which
  10. customevaporate the solvent in the eluent

Sources & evidence

ORD record
ord-84ccef2367294d3c860574546c009b6d
Source dataset
uspto-grants-2016_06
Patent number
US09359298B2

Reaction notes

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