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

HRID 720156Notes

Reaction equation

HRID 720156 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-fb3f316c83464af7bb2c4b68dd61b2f2
Source dataset
uspto-grants-2006_11
Patent number
US07132533B2

Reaction notes

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