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

HRID 1710699Notes

Reaction equation

HRID 1710699 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].[Sn:21](Cl)([CH2:30][CH2:31][CH2:32][CH3:33])([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:22][CH2:23][CH2:24][CH3:25]>C1COCC1.C(OCC)(=O)C>[CH2:30]([Sn:21]([CH2:22][CH2:23][CH2:24][CH3:25])([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, 8.4 mL, 14.3 mmol) was added dropwise over 30 min. to a stirred solution of 2-(triisopropylsilyl)-1,3-oxazole* (3 g, 13 mmol) in THF (75 mL) at −78° C. under argon. The solution was allowed to stir for 20 min. at −78° C. and Bu3SnCl (5.2 mL, 19.5 mmol) was then added over 20 min. The reaction mixture was warmed up to room temperature and stirred for an additional 16 h. The reaction was diluted with ethyl acetate and washed with water. The organic layer was dried over 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. *Prepared according to Ross A, et al. Tetrahedron Letters 2002, 43, 935.

Workup

  1. temperatureThe reaction mixture was warmed up to room temperature
  2. stirringstirred for an additional 16 h
  3. washwashed with water
  4. dry with materialThe organic layer was dried over 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-ab3b1d29ba314787baf7953776fdbdd7
Source dataset
uspto-grants-2010_09
Patent number
US07790728B2

Reaction notes

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