Tributyltin Chloride → Tributyl(2,3-dihydrofuran-5-yl)stannane

HRID 1356086Notes

Reaction equation

HRID 1356086 reaction equation
[O:1]1[CH:5]=[CH:4][CH2:3][CH2:2]1.C([Li])(C)(C)C.[CH2:11]([Sn:15](Cl)([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH2:18][CH3:19])[CH2:12][CH2:13][CH3:14]>C1COCC1>[CH2:20]([Sn:15]([CH2:11][CH2:12][CH2:13][CH3:14])([CH2:16][CH2:17][CH2:18][CH3:19])[C:5]1[O:1][CH2:2][CH2:3][CH:4]=1)[CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 709342,3-DihydrofuranHCID 178418306HCID 178418306, compound

Product 1

HCID 14323397Tributyl(2,3-dihydrofuran-5-yl)stannaneYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 0.35 ml (7.13 mmol) 2,3-dihydrofuran in 10 ml dry THF under argon at −78° C. was added 4.7 ml (7.2 mmol) tert-butyllithium solution (1.5M in pentane) and stirring continued for 5 minutes at −78° C. and 15 minutes at 0° C. The reaction mixture was then recooled to −78° C. and 1.92 ml (7.13 mmol) tributyltin chloride added dropwise and stirring continued for 16 hours at room temperature. The reaction mixture was partitioned between ether and water. The organic phase was then washed with brine, dried over sodium sulfate, and concentrated in vacuo to afford 2.37 g (93%) tributyl-(4,5-dihydro-furan-2-yl)-stannane as a yellow liquid which was used in the next step without further purification. EI-MS m/e (%): cluster at 303 ([M—C4H9]+, 100).

Workup

  1. customwas then recooled to −78° C.
  2. stirringstirring
  3. waitcontinued for 16 hours at room temperature
  4. customThe reaction mixture was partitioned between ether and water
  5. washThe organic phase was then washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bf736780f4214ec38bad0c1e6b91dfe3
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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