Styrene → 5-[7-(4-Cyanophenoxy)heptyl]-3-methylisoxazole

HRID 1905472Notes

Reaction equation

HRID 1905472 reaction equation
[Li].C(NC(C)C)(C)C.C=CC1C=CC=CC=1.[CH3:17][C:18]1[CH:22]=[C:21]([CH3:23])[O:20][N:19]=1.Br[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][O:31][C:32]1[CH:39]=[CH:38][C:35]([C:36]#[N:37])=[CH:34][CH:33]=1>O1CCCC1>[C:36]([C:35]1[CH:38]=[CH:39][C:32]([O:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:23][C:21]2[O:20][N:19]=[C:18]([CH3:17])[CH:22]=2)=[CH:33][CH:34]=1)#[N:37]

Participants

7

Reactant 5

HCID 7501StyreneHCID 7912DiisopropylamineHCID 93123,5-DimethylisoxazoleHCID 3028194Lithium2×HCID 134508844-[(6-Bromohexyl)oxy]benzonitrile

Product 1

HCID 52712085-[7-(4-Cyanophenoxy)heptyl]-3-methylisoxazoleYield 30.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
25 °C

Procedure

To a suspension of 301 mg of lithium wire (1/4 inch portions) in 10 ml of tetrahydrofuran under nitrogen was added 6.72 ml of diisopropylamine and 3.44 ml of styrene while maintaining the temperature at 25° C. The mixture was stirred until all the lithium had dissolved (about four hours) and then cooled to -55° C. 3,5-Dimethylisoxazole (4.3 g) in 10 ml of tetrahydrofuran was then added dropwise and the mixture stirred for an hour at -55° C. 4-(6-Bromohexyloxy)benzonitrile (12 g) in 10 ml of tetrahydrofuran was then added dropwise over a period of one hour, and the mixture was allowed to warm to room temperature and stirred for three days. The solvent was removed in vacuo, the residue treated with 5% ammonium chloride solution and extracted with ether. The ether extracts were dried and concentrated, and the residue subjected to high pressure liquid chromatography with ether-hexane (1:1) mixture to give 3.9 g of 5-[7-(4-cyanophenoxy)heptyl]-3-methylisoxazole, used directly in the next reaction.

Workup

  1. dissolutionhad dissolved (about four hours)
  2. temperaturecooled to -55° C
  3. temperatureto warm to room temperature
  4. stirringstirred for three days
  5. customThe solvent was removed in vacuo
  6. additionthe residue treated with 5% ammonium chloride solution
  7. extractionextracted with ether
  8. dry with materialThe ether extracts were dried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-6c4590d495864917a2f6c1390d81b041
Source dataset
uspto-grants-1989_06
Patent number
US04843087

Reaction notes

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