Tributyltin Chloride → 5-(Tributylstannyl)-2-(triisopropylsilyl)-1,3-oxazole

HRID 2264194Notes

Reaction equation

HRID 2264194 reaction equation
[Li]C(C)(C)C.[CH:6]([Si:9]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[C:10]1[O:11][CH:12]=[CH:13][N:14]=1)([CH3:8])[CH3:7].[CH2:21]([Sn:25](Cl)([CH2:30][CH2:31][CH2:32][CH3:33])[CH2:26][CH2:27][CH2:28][CH3:29])[CH2:22][CH2:23][CH3:24]>O1CCCC1.C(OCC)(=O)C>[CH2:30]([Sn:25]([CH2:21][CH2:22][CH2:23][CH3:24])([CH2:26][CH2:27][CH2:28][CH3:29])[C:12]1[O:11][C:10]([Si:9]([CH:6]([CH3:8])[CH3:7])([CH:15]([CH3:17])[CH3:16])[CH:18]([CH3:20])[CH3:19])=[N:14][CH:13]=1)[CH2:31][CH2:32][CH3:33]

Participants

6

Reactant 3

HCID 15096Tributyltin ChlorideHCID 595960162-(Tris(propan-2-yl)silyl)-1,3-oxazoleHCID 178418306HCID 178418306, compound

Product 1

HCID 114971955-(Tributylstannyl)-2-(triisopropylsilyl)-1,3-oxazole

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

tert-BuLi (1.7M in n-pentane, 8.4 mL, 14.3 mmol) was added dropwise over (approximately) 30 minutes to a stirred solution of 2-triisopropylsilyloxazole (3 g, 13 mmol) in tetrahydrofuran (75 mL) at −78° C. under argon. The solution was allowed to stir for 20 minutes at −78° C. and tributyltin chloride (5.2 mL, 19.5 mmol) was then added over 20 minutes. The reaction mixture was warmed to room temperature and stirred for an additional 16 hours. The reaction was diluted with ethyl acetate, washed with water and the organic layer was dried (MgSO4) and concentrated under reduced pressure. The crude product was dissolved in n-pentane, filtered through Celite® and the solvent evaporated to give the title compound in quantitative yield as a pale-yellow oily residue, which was used without further purification in the next step.

Workup

  1. temperatureThe reaction mixture was warmed to room temperature
  2. stirringstirred for an additional 16 hours
  3. washwashed with water
  4. dry with materialthe organic layer was dried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe crude product was dissolved in n-pentane
  7. filtrationfiltered through Celite®
  8. customthe solvent evaporated

Sources & evidence

ORD record
ord-5b3bbb8e10c94c7986edd4b68abe17ea
Source dataset
uspto-grants-2010_12
Patent number
US07855202B2

Reaction notes

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