Tetrahydrofuran → HCID 59259720, compound

HRID 642959Notes

Reaction equation

HRID 642959 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([CH3:10])[CH2:6][CH2:5]1.O1CCCC1.[H-].[Na+].[CH2:18]([Sn:22]([CH2:29][CH2:30][CH2:31][CH3:32])([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:23]I)[CH2:19][CH2:20][CH3:21]>C(OCC)(=O)C.O.CN(C)C=O>[CH3:10][N:7]1[CH2:8][CH2:9][N:4]([CH2:3][CH2:2][O:1][CH2:23][Sn:22]([CH2:18][CH2:19][CH2:20][CH3:21])([CH2:29][CH2:30][CH2:31][CH3:32])[CH2:25][CH2:26][CH2:27][CH3:28])[CH2:5][CH2:6]1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 2311841-(2-Hydroxyethyl)-4-methylpiperazineHCID 10862926Tributyl(iodomethyl)stannane

Product 1

HCID 59259720HCID 59259720, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 1-(2-hydroxyethyl)-4-methylpiperazine (1.0 g, 6.9 mmol) and tetrahydrofuran (15 ml) was added sodium hydride (60%, 277 mg, 6.9 mmol) at 0° C. (external temperature), and the reaction mixture was stirred at room temperature for 30 minutes. Then, to the reaction mixture was added dropwise a mixture of tributyl-iodomethyl-tin (2.0 g, 4.6 mmol) and N,N-dimethylformamide (15 ml) at 0° C. (external temperature). Then, the reaction mixture was stirred at room temperature for 1.5 hours. To the reaction mixture were added water and ethyl acetate, and the organic layer was separated. The organic layer was washed with water and an aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=10:1, NH silica gel) to obtain the title compound (1.9 g, 4.2 mmol, 92%).

Workup

  1. additionThen, to the reaction mixture was added dropwise
  2. stirringThen, the reaction mixture was stirred at room temperature for 1.5 hours
  3. customthe organic layer was separated
  4. washThe organic layer was washed with water
  5. dry with materialan aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=10:1, NH silica gel)

Sources & evidence

ORD record
ord-3a1d4e123ddc4ad48ba511ec49e9014a
Source dataset
uspto-grants-2010_04
Patent number
US07696347B2

Reaction notes

Loading…