Tetrahydrofuran → Tributyl(iodomethyl)stannane

HRID 642952Notes

Reaction equation

HRID 642952 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCCC1.[I:25]N1C(=O)CCC1=O.[CH2:33]([Sn:37]([CH2:46]O)([CH2:42][CH2:43][CH2:44][CH3:45])[CH2:38][CH2:39][CH2:40][CH3:41])[CH2:34][CH2:35][CH3:36]>O.C(OCC)C>[CH2:33]([Sn:37]([CH2:42][CH2:43][CH2:44][CH3:45])([CH2:38][CH2:39][CH2:40][CH3:41])[CH2:46][I:25])[CH2:34][CH2:35][CH3:36]

Participants

7

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 11776TriphenylphosphineHCID 120273N-IodosuccinimideHCID 41935931-(Tributylstannyl)methanol

Product 1

HCID 10862926Tributyl(iodomethyl)stannaneYield 77,777.797%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of triphenylphosphine (70 g, 0.27 mol) and tetrahydrofuran (500 ml) was added dropwise a mixture of N-iodosuccinimide (60 g, 0.27 mmol) and tetrahydrofuran (500 ml) at 0° C. (external temperature). Then, the reaction mixture was stirred at 0° C. (external temperature) for 30 minutes. To the mixture was added dropwise tributylstannyl-methanol (71 g, 0.22 mol) at 0° C. (external temperature). Then, the reaction mixture was stirred at 0° C. (external temperature) for 20 minutes. The reaction mixture was stirred at room temperature overnight. To the reaction mixture were added diethyl ether and water, and the organic layer was separated. The organic layer was sequentially washed with an aqueous saturated sodium thiosulfate solution and an aqueous saturated sodium chloride solution. The organic layer was separated, and the solvent was distilled off under reduced pressure. To the residue was added heptane (400 ml), followed by filtration. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (heptane) to obtain the title compound (90 g, 0.21 mol, 94%).

Workup

  1. additionwas added dropwise
  2. stirringThen, the reaction mixture was stirred at 0° C. (external temperature) for 20 minutes
  3. stirringThe reaction mixture was stirred at room temperature overnight
  4. customthe organic layer was separated
  5. washThe organic layer was sequentially washed with an aqueous saturated sodium thiosulfate solution
  6. customThe organic layer was separated
  7. distillationthe solvent was distilled off under reduced pressure
  8. additionTo the residue was added heptane (400 ml)
  9. filtrationfollowed by filtration
  10. distillationThe solvent was distilled off under reduced pressure
  11. customthe residue was purified by silica gel column chromatography (heptane)

Sources & evidence

ORD record
ord-47763517336b4fe4b7c75c8afdaede3c
Source dataset
uspto-grants-2010_04
Patent number
US07696347B2

Reaction notes

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