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

HRID 1410129Notes

Reaction equation

HRID 1410129 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-40ad9d906b3b4c51acc6df0bdb45cdc1
Source dataset
uspto-grants-2014_12
Patent number
US08921402B2

Reaction notes

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