Tributyltin Chloride → 5-(Tributylstannyl)-2-(trimethylsilyl)thiazole

HRID 660724Notes

Reaction equation

HRID 660724 reaction equation
[Li]CCCC.[CH3:6][Si:7]([CH3:14])([CH3:13])[C:8]1[S:9][CH:10]=[CH:11][N:12]=1.[CH2:15]([Sn:19](Cl)([CH2:24][CH2:25][CH2:26][CH3:27])[CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH3:18]>CCOCC>[CH2:24]([Sn:19]([CH2:15][CH2:16][CH2:17][CH3:18])([CH2:20][CH2:21][CH2:22][CH3:23])[C:10]1[S:9][C:8]([Si:7]([CH3:14])([CH3:13])[CH3:6])=[N:12][CH:11]=1)[CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 5884532-TrimethylsilylthiazoleHCID 178418339Butyllithium

Product 1

HCID 225941385-(Tributylstannyl)-2-(trimethylsilyl)thiazole

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
-78 °C

Procedure

To a solution of n-BuLi (2.5M in hexane, 6.0 mL, 15 mmol) in ether (60 mL) at −78° C. is added a solution of 2-(trimethylsilyl)thiazole (2.0 mL, 12.5 mmol) in ether (20 mL) dropwise. The mixture is stirred at −78° C. for 1 h then tributyltin chloride (4.04 mL, 15 mmol) in ether (25 mL) is added dropwise and stirring is continued at −78° C. for 1 h. The reaction mixture is washed with saturated NaHCO3, dried over anhydrous MgSO4 and concentrated to afford the title compound as a yellow oil which used in the next step without further purification: 1H NMR (CDCl3) δ 0.41 (s, 9H), 0.90 (t, J=8 Hz, 9H), 1.14 (q, 6H), 1.13 (q, 6H), 1.54 (m, 6H), 8.06 (s, 1H); (M+1)+=447.

Workup

  1. stirringstirring
  2. waitis continued at −78° C. for 1 h
  3. washThe reaction mixture is washed with saturated NaHCO3
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e674b243fc3043b689bfc1f41f8c537a
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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