Nitroethane → 3-Methyl-5-(tributylstannyl)isoxazole

HRID 2375122Notes

Reaction equation

HRID 2375122 reaction equation
[N+:1]([CH2:4][CH3:5])([O-])=[O:2].C1(N=C=O)C=CC=CC=1.[C:15]([Sn:17]([CH2:26][CH2:27][CH2:28][CH3:29])([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19][CH2:20][CH3:21])#[CH:16].CCN(CC)CC>C1C=CC=CC=1>[CH3:5][C:4]1[CH:16]=[C:15]([Sn:17]([CH2:22][CH2:23][CH2:24][CH3:25])([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:26][CH2:27][CH2:28][CH3:29])[O:2][N:1]=1

Participants

6

Reactant 4

HCID 6587NitroethaneHCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 621176Ethynyltributyltin

Product 1

HCID 27632553-Methyl-5-(tributylstannyl)isoxazoleYield 85%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution of nitroethane and phenyl isocynate in 8 ml of benzene was stirred at 50° C. for 5 minutes before ethynyltri-n-butyltin in 8 ml of benzene containing one droplet of Et3N was added. The mixture was stirred at 50° C. for 14 hours. The reaction mixture was then quenched with water and filtered through celite. The filtrate was extracted with EtOAc, dried with Na2SO4. Silica Chromatography using Hexance/EtOAc afforded 3-methyl-5-(tributylstannyl)isoxazole, 6.30 g, 85% yield.

Workup

  1. additionwas added
  2. customThe reaction mixture was then quenched with water
  3. filtrationfiltered through celite
  4. extractionThe filtrate was extracted with EtOAc
  5. dry with materialdried with Na2SO4

Sources & evidence

ORD record
ord-e2f0ebba4c7f46ce92d49d36c2357dff
Source dataset
uspto-grants-2008_12
Patent number
US07462713B2

Reaction notes

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