Tributyltin Chloride → 3,5-Dimethyl-4-(tributylstannyl)isoxazole

HRID 242180Notes

Reaction equation

HRID 242180 reaction equation
[Li]CCCC.I[C:7]1[C:8]([CH3:13])=[N:9][O:10][C:11]=1[CH3:12].[CH2:14]([Sn:18](Cl)([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:19][CH2:20][CH2:21][CH3:22])[CH2:15][CH2:16][CH3:17]>C1COCC1>[CH3:13][C:8]1[C:7]([Sn:18]([CH2:19][CH2:20][CH2:21][CH3:22])([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:14][CH2:15][CH2:16][CH3:17])=[C:11]([CH3:12])[O:10][N:9]=1

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 6138834-Iodo-3,5-dimethyl-1,2-oxazoleHCID 178418339Butyllithium

Product 1

HCID 150622153,5-Dimethyl-4-(tributylstannyl)isoxazoleYield 39.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-BuLi (1.6 M solution in hexanes, 6 mL, 9.6 mmol) was added to a cooled (−78° C.) solution of 4-iodo-3,5-dimethylisoxazole (1.47 g, 6.60 mmol) in THF (24 mL) under nitrogen. After 15 min, tributyltin chloride (26 mL, 9.60 mmol) was added and the reaction was stirred over night while warming to room temperature. The reaction was quenched by 1 M HCl, CH2Cl2 was added, the phases separated and the solvent were evaporated. The residue was purified by flash chromatography with heptane:CH2Cl2 (75:25-0:100) to give 3,5-dimethyl-4-(tributylstannyl)isoxazole (1.00 g, 39%).

Workup

  1. customThe reaction was quenched by 1 M HCl, CH2Cl2
  2. additionwas added
  3. customthe phases separated
  4. customthe solvent were evaporated
  5. customThe residue was purified by flash chromatography with heptane:CH2Cl2 (75:25-0:100)

Sources & evidence

ORD record
ord-9a66aca1b66c45cba184f2469340e70f
Source dataset
uspto-grants-2014_02
Patent number
US08653112B2

Reaction notes

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