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

HRID 219099Notes

Reaction equation

HRID 219099 reaction equation
[N+:1]([CH2:4][CH3:5])([O-])=[O:2].C1(N=C=O)C=CC=CC=1.C(N(CC)CC)C.[CH2:22]([Sn:26]([CH2:33][CH2:34][CH2:35][CH3:36])([CH2:29][CH2:30][CH2:31][CH3:32])[C:27]#[CH:28])[CH2:23][CH2:24][CH3:25]>C1C=CC=CC=1.O>[CH3:5][C:4]1[CH:28]=[C:27]([Sn:26]([CH2:22][CH2:23][CH2:24][CH3:25])([CH2:33][CH2:34][CH2:35][CH3:36])[CH2:29][CH2:30][CH2:31][CH3:32])[O:2][N:1]=1

Participants

7

Reactant 4

HCID 6587NitroethaneHCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 621176Ethynyltributyltin

Product 1

HCID 27632553-Methyl-5-(tributylstannyl)isoxazole

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of nitroethane (0.0952 ml, 1.33 mmol) in benzene (2 mL) was added phenyl isocyanate (0.291 ml, 2.66 mmol). The solution was stirred at 50° C. for ten minutes followed by the addition of triethylamine (0.00925 ml, 0.0666 mmol) and tributyl(ethynyl)stannane (0.365 ml, 1.27 mmol). The mixture was left to stir at 50° C. overnight. The solution was diluted with water and filtered though a celite plug, the resulting filtrate was extracted with toluene. Organic extracts were dried over magnesium sulfate and filtered then concentrated to yield the product as a yellow oil.

Workup

  1. waitThe mixture was left
  2. stirringto stir at 50° C. overnight
  3. filtrationfiltered though a celite plug
  4. extractionthe resulting filtrate was extracted with toluene
  5. dry with materialOrganic extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationthen concentrated

Sources & evidence

ORD record
ord-295f55abec3b457c9cf4d749cdd7492f
Source dataset
uspto-grants-2012_06
Patent number
US08198448B2

Reaction notes

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