Tetrahydrofuran → Tributyl-cyclobutoxymethyl-tin

HRID 640498Notes

Reaction equation

HRID 640498 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 (250 mg, 7.0 mmol, 66% in oil) and tetrahydrofuran (20 mL) were added cyclobutanol (0.55 mL, 7.0 mmol) and N,N-dimethylformamide (20 mL) at 0° C., and then the reaction mixture was stirred for 40 minutes at room temperature. The tributyl-iodomethyl-tin (2.0 g, 4.6 mmol) described in Manufacturing Example 197-2-2 was added dropwise to the reaction mixture at 0° C., and then the reaction mixture was stirred overnight at room temperature. Heptane and water were added to the reaction mixture, and the organic layer was separated. The organic layer was washed and saturated aqueous sodium chloride, and was concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=20:1) to obtain the title compound (1.6 g, 92%).

Workup

  1. additionwas added dropwise to the reaction mixture at 0° C.
  2. stirringthe reaction mixture was stirred overnight at room temperature
  3. customthe organic layer was separated
  4. washThe organic layer was washed
  5. concentrationsaturated aqueous sodium chloride, and was concentrated under a reduced pressure
  6. customThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-90a4e6f5ec424c15be7c69dd330c2f63
Source dataset
uspto-grants-2010_04
Patent number
US07691882B2

Reaction notes

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