Benzene → HCID 58260902, compound

HRID 1897627Notes

Reaction equation

HRID 1897627 reaction equation
C1C=CC=CC=1.[CH2:7]([C:9]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][CH3:21])[C:10]=1/[N:11]=[CH:12]/[CH:13]([CH3:15])[CH3:14])[CH3:8].C([N-]C(C)C)(C)C.[Li+:29]>CCCCC>[CH2:7]([C:9]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][CH3:21])[C:10]=1[N-:11][CH:12]=[C:13]([CH3:15])[CH3:14])[CH3:8].[Li+:29]

Participants

5

Reactant 3

HCID 241BenzeneHCID 2724682Lithium diisopropylamideHCID 178436228HCID 178436228, compound

Product 1

HCID 58260902HCID 58260902, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Conditions

Temperature
50 °C

Procedure

Benzene (70 mL) and compound A (6.63 g, 32.6 mmol) were combined. Solid lithium diisopropylamide (4.01 g, 37.4 mmol) was then added. The mixture was heated to 50° C. to form a cloudy red-orange solution. After a few hours the solution was filtered through diatomaceous earth to afford a clear yellow solution. The volatiles were evaporated to give a yellow solid. Pentane (15 mL) was added and the mixture was stirred briefly and then cooled to −10° C. overnight. The product was then collected on a glass frit and washed with pentane (2×20 mL) to yield 5.50 g of compound B (80.6%) as a white solid that was dried under reduced pressure and used without further characterization.

Workup

  1. customto form a cloudy red-orange solution
  2. filtrationAfter a few hours the solution was filtered through diatomaceous earth
  3. customto afford a clear yellow solution
  4. customThe volatiles were evaporated
  5. customto give a yellow solid
  6. temperaturecooled to −10° C. overnight
  7. customThe product was then collected on a glass frit
  8. washwashed with pentane (2×20 mL)

Sources & evidence

ORD record
ord-c5fe0c7dcc6047d2822ed3f91adaf8f0
Source dataset
uspto-grants-2013_08
Patent number
US08519147B2

Reaction notes

Loading…