Hexane → HCID 18509434, compound

HRID 1356832Notes

Reaction equation

HRID 1356832 reaction equation
[CH2:1]([Li])[CH2:2]CC.[CH3:6]CCCCC.[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:23]=[C:24]([C:28](=O)[CH3:29])[CH:25]=[CH:26][CH:27]=1)[CH3:20]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[C:13]([C:14]1[CH:2]=[CH:1][C:17]([CH2:18][N:19]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([CH3:6])=[CH2:29])[CH:23]=2)[CH3:20])=[CH:16][CH:15]=1)([CH3:32])([CH3:31])[CH3:12]

Participants

6

Reactant 3

HCID 8058HexaneHCID 12069881HCID 12069881, compoundHCID 178418339Butyllithium

Product 1

HCID 18509434HCID 18509434, compoundYield 57.4%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Methyl triphenylphosphonium bromide (1.97 g; 5.51 mmol) was suspended in tetrahydrofuran (15 ml). While the suspension was stirred under nitrogen atmosphere at room temperature, n-butyl lithium in n-hexane (1.68 M: 3.9 ml; 6.60 mmol) was added dropwise. After the reaction mixture turned deep red, the mixture was cooled in an ice bath, and Compound 1 (1.42 g; 4.59 mmol) in tetrohydrofuran (15 ml) was added dropwise thereto. After completion of the addition, the mixture was removed from the ice bath, and stirred for 30 minutes at room temperature. Reaction was stopped by pouring the mixture into ice/water, followed by extraction with diethyl ether (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=10:1), to thereby yield 0.81 g of the target compound as yellow oily matter (yield: 57.4%).

Workup

  1. temperaturethe mixture was cooled in an ice bath
  2. additionAfter completion of the addition
  3. customthe mixture was removed from the ice bath
  4. stirringstirred for 30 minutes at room temperature
  5. customReaction
  6. extractionfollowed by extraction with diethyl ether (100 ml)
  7. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution
  8. dry with materialwith saturated brine, and dried over anhydrous sodium sulfate
  9. customThe solvent was evaporated under reduced pressure
  10. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-29a0a920d33a4ceca85d759c256b58fa
Source dataset
uspto-grants-2003_07
Patent number
US06586633B1

Reaction notes

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