Hexane → HCID 18509478, compound

HRID 1356840Notes

Reaction equation

HRID 1356840 reaction equation
[C:1]([C:5]1[CH:21]=[CH:20][C:8]([CH2:9][N:10]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15](Br)[CH:14]=2)[CH3:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.CCCCCC.[CH3:33][CH:34]([CH3:38])[C:35](=[O:37])[CH3:36].[Cl-].[NH4+]>O1CCCC1>[C:1]([C:5]1[CH:21]=[CH:20][C:8]([CH2:9][N:10]([CH2:12][C:13]2[CH:14]=[C:15]([C:35]([OH:37])([CH:34]([CH3:38])[CH3:33])[CH3:36])[CH:16]=[CH:17][CH:18]=2)[CH3:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 8058HexaneHCID 112513-Methyl-2-butanoneHCID 25517Ammonium ChlorideHCID 18509495HCID 18509495, compoundHCID 178418339Butyllithium

Product 1

HCID 18509478HCID 18509478, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-40 °C

Procedure

Compound 78 (2.00 g; 5.78 mmol) was dissolved in tetrahydrofuran (20 ml). While the solution was stirred at −40° C. under nitrogen atmosphere, n-butyl lithium in n-hexane (1.56 M: 3.7 ml; 5.8 mmol) was added dropwise. After completion of the addition, the mixture was cooled to −75° C., an 3-methyl-2-butanone (2.00 g) in a small amount of tetrahydrofuran was added dropwise thereto. The resultant mixture was gradually brought to room temperature, and the reaction was stopped by dropwise addition of saturated aqueous ammonium chloride solution, followed by extraction with diethyl ether (100 ml). The organic layer was washed with saturated brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1), to thereby yield 0.86 g of the target compound as brown oily matter (yield: 43.3%).

Workup

  1. additionAfter completion of the addition
  2. temperaturethe mixture was cooled to −75° C.
  3. customwas gradually brought to room temperature
  4. extractionfollowed by extraction with diethyl ether (100 ml)
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-5bae4cffa72646d5a3e000d9b94dfc0b
Source dataset
uspto-grants-2003_07
Patent number
US06586633B1

Reaction notes

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