Hexane → HCID 18182202, compound

HRID 1359408Notes

Reaction equation

HRID 1359408 reaction equation
CCCCCC.C([Li])CCC.[CH2:12]([C:19]1[S:20][CH:21]=[CH:22][C:23]=1[C:24]#[CH:25])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[N:26]12[CH2:33][CH2:32][CH:29]([CH2:30][CH2:31]1)[C:28](=[O:34])[CH2:27]2>O.O1CCCC1>[CH2:12]([C:19]1[S:20][CH:21]=[CH:22][C:23]=1[C:24]#[C:25][C:28]1([OH:34])[CH:29]2[CH2:32][CH2:33][N:26]([CH2:31][CH2:30]2)[CH2:27]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 8058HexaneHCID 195073-QuinuclidinoneHCID 18182189HCID 18182189, compoundHCID 178418339Butyllithium

Product 1

HCID 18182202HCID 18182202, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

0.200 ml of a hexane solution containing 1.8 mol of butyl lithium was added dropwise to a mixture of 45.2 mg of 2-benzyl-3-ethynyl-thiophene and 1 ml of tetrahydrofuran at −78° C., followed by stirring at the same temperature for 20 hours. A solution of 0.5 ml of tetrahydrofuran containing 39.9 mg of 3-quinuclidinone was added dropwise to the reaction solution at the same temperature, followed by stirring and then at room temperature for 4 hours. 0.5 ml of water and NH-silica gel were added to the reaction solution, and the solvent was removed. The residue was subjected to NH-silica gel column chromatography using ethyl acetate, to give 39.5 mg of the target compound.

Workup

  1. stirringby stirring
  2. waitat room temperature for 4 hours
  3. customthe solvent was removed

Sources & evidence

ORD record
ord-9a54fb053ed64bf1aae3bdf65af246a9
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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