Oxazole → 2-(Tri-n-butylstannyl)oxazole

HRID 1356105Notes

Reaction equation

HRID 1356105 reaction equation
[O:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C([Li])CCC.[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:2]1[O:1][CH:5]=[CH:4][N:3]=1)[CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 9255OxazoleHCID 15096Tributyltin ChlorideHCID 178418339Butyllithium

Product 1

HCID 154861832-(Tri-n-butylstannyl)oxazoleYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1.00 g (14.5 mmol) oxazole in 25 ml dry THF under argon at −78° C. was added 9.14 ml (14.6 mmol) n-butyllithium solution (1.6M in hexane) and stirring continued for 30 minutes at −78° C. 3.91 ml (14.5 mmol) tributyltin chloride was then added dropwise and stirring continued for 15 minutes at −78° C. and for 1 hour at room temperature. The reaction mixture was then concentrated in vacuo and the residue resuspended in 50 ml hexane. The insoluble lithium salts were removed by filtration and the filtrate was concentrated in vacuo to afford 4.90 g (95%) 2-tributylstannanyl-oxazole as a light yellow liquid which was used in the next step without further purification. 1H NMR 6 (CDCl3, 250 MHz): 7.84 (1H, s), 7.18 (1H, s), 1.67-1.53 (6H, m), 1.42-1.29 (6H, m), 1.20 (6H, t, J=8 Hz), 0.89 (9H, t, J=7 Hz).

Workup

  1. stirringstirring
  2. waitcontinued for 15 minutes at −78° C. and for 1 hour at room temperature
  3. concentrationThe reaction mixture was then concentrated in vacuo
  4. customThe insoluble lithium salts were removed by filtration
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-08940f6afd2b4f5188425848919be66c
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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