Hexane → HCID 18509398, compound

HRID 1356844Notes

Reaction equation

HRID 1356844 reaction equation
[CH2:1]([Li])[CH2:2]CC.[CH3:6]CCCCC.Cl.[CH3:13][C:14]([CH3:34])([CH3:33])[C:15]#[C:16]/[CH:17]=[CH:18]/[CH2:19][N:20]([CH2:22][C:23]1[CH:28]=[C:27](C)[CH:26]=[C:25]([C:30]([CH3:32])=[CH2:31])[CH:24]=1)[CH3:21]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1C=CC=CC=1>[C:14]([C:15]1[CH:16]=[CH:17][C:18]([CH2:19][N:20]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:30]([CH2:32][CH3:6])=[CH2:31])[CH:24]=2)[CH3:21])=[CH:2][CH:1]=1)([CH3:13])([CH3:33])[CH3:34]

Participants

6

Reactant 3

HCID 8058HexaneHCID 18509523HCID 18509523, compoundHCID 178418339Butyllithium

Product 1

HCID 18509398HCID 18509398, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 241BenzeneSolvent2×

Procedure

Methyl triphenylphosphonium bromide (0.18 g; 4.94×10−1 mmol) was added to benzene (7 ml). While the mixture was stirred under nitrogen atmosphere at room temperature, n-butyl lithium in n-hexane (1.56 M: 0.32 ml; 5.00×10−1 mmol) was added dropwise. The mixture was stirred for 5 minutes, and Compound 19 (0.08 g; 2.47×10−1 mmol) in benzene (5 ml) was added dropwise thereto, followed by heating under reflux for 2 hours. The mixture was brought to room temperature, and the reaction was stopped by pouring the mixture into ice/water, followed by extraction with benzene (100 ml). The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1), to thereby yield 0.05 g of the target compound as colorless transparent oily matter (yield: 63%).

Workup

  1. stirringThe mixture was stirred for 5 minutes
  2. temperatureby heating
  3. temperatureunder reflux for 2 hours
  4. customwas brought to room temperature
  5. extractionfollowed by extraction with benzene (100 ml)
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-095a4350b07e42d1aebcfdee0847c10d
Source dataset
uspto-grants-2003_07
Patent number
US06586633B1

Reaction notes

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