Hexane → HCID 18509433, compound

HRID 1356835Notes

Reaction equation

HRID 1356835 reaction equation
[CH2:1]([Li])[CH2:2]CC.CCCCCC.[CH3:12][C:13]([CH3:32])([CH3:31])[C:14]#[C:15]/[CH:16]=[CH:17]\[CH2:18][N:19]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([CH3:30])=C)[CH:23]=1)[CH3:20]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1C=CC=CC=1>[C:13]([C:14]1[CH:15]=[CH:16][C:17]([CH2:18][N:19]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH:28]=[CH2:30])[CH:23]=2)[CH3:20])=[CH:2][CH:1]=1)([CH3:12])([CH3:31])[CH3:32]

Participants

6

Reactant 3

HCID 8058HexaneHCID 86759054HCID 86759054, compoundHCID 178418339Butyllithium

Product 1

HCID 18509433HCID 18509433, compoundYield 49.4%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 241BenzeneSolvent2×

Procedure

Methyl triphenylphosphonium bromide (1.07 g; 3.00 mmol) was added to benzene (20 ml). While the mixture was stirred under nitrogen atmosphere at room temperature, n-butyl lithium in n-hexane (1.56 M: 1.9 ml; 3.00 mmol) was added dropwise. The mixture was stirred for 10 minutes, and Compound 5 (0.59 g; 2.00 mmol) in benzene (15 ml) was added dropwise thereto, followed by stirring for 3 hours at room temperature. Reaction was stopped by pouring the mixture into ice/water, followed by extraction with benzene (100 ml). The organic layer was washed with saturated aqueous sodium bicarbonate solution and then 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=20:1), to thereby yield 0.29 g of the target compound as pale yellow oily matter (yield: 49.4%).

Workup

  1. stirringThe mixture was stirred for 10 minutes
  2. stirringby stirring for 3 hours at room temperature
  3. customReaction
  4. extractionfollowed by extraction with benzene (100 ml)
  5. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution
  6. dry with materialwith saturated brine, and dried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-ec32a105ae7e4da1950a14011657da70
Source dataset
uspto-grants-2003_07
Patent number
US06586633B1

Reaction notes

Loading…