Tetrahydrofuran → Tributyl-cyclobutoxymethyl-tin

HRID 642954Notes

Reaction equation

HRID 642954 reaction equation
[H-].[Na+].[O:3]1[CH2:7][CH2:6][CH2:5][CH2:4]1.C1(O)CCC1.[CH2:13]([Sn:17]([CH2:24][CH2:25][CH2:26][CH3:27])([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:18]I)[CH2:14][CH2:15][CH3:16]>O.CCCCCCC.CN(C)C=O>[CH2:24]([Sn:17]([CH2:13][CH2:14][CH2:15][CH3:16])([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:18][O:3][CH:7]1[CH2:6][CH2:5][CH2:4]1)[CH2:25][CH2:26][CH3:27]

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 76218CyclobutanolHCID 10862926Tributyl(iodomethyl)stannane

Product 1

HCID 22273693Tributyl-cyclobutoxymethyl-tinYield 92%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8900HeptaneSolvent

Procedure

To a mixture of sodium hydride (66%, 250 mg, 7.0 mmol) and tetrahydrofuran (20 ml) were added cyclobutanol (0.55 ml, 7.0 mmol) and N,N-dimethylformamide (20 ml) at 0° C. (external temperature). Then, the reaction mixture was stirred at room temperature for 40 minutes. To the reaction mixture was added dropwise tributyl-iodomethyl-tin (2.0 g, 4.6 mmol) at 0° C. (external temperature). Then, the reaction mixture was stirred at room temperature overnight. To the reaction mixture were added heptane and water, and the organic layer was separated. The organic layer was washed with an aqueous saturated sodium chloride solution, and then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethylacetate=20:1) to obtain the title compound (1.6 g, 4.3 mmol, 92%).

Workup

  1. stirringThen, the reaction mixture was stirred at room temperature overnight
  2. customthe organic layer was separated
  3. washThe organic layer was washed with an aqueous saturated sodium chloride solution
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (heptane:ethylacetate=20:1)

Sources & evidence

ORD record
ord-9fcc3472d34d4be384511481d70efff6
Source dataset
uspto-grants-2010_04
Patent number
US07696347B2

Reaction notes

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