(E)-1-Phenyl-1,3-butadiene → 2-Methyl-3-(2-naphthalenyl)-5-(2-trans-phenylethenyl)-3-(1H-1,2,4-triazol-1-ylmethyl)isoxazolidine

HRID 867962Notes

Reaction equation

HRID 867962 reaction equation
[N:1]1([CH2:6][C:7]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=2)=[N+:8]([O-:10])[CH3:9])[CH:5]=[N:4][CH:3]=[N:2]1.[C:21]1(/[CH:27]=[CH:28]/[CH:29]=[CH2:30])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(OCC)(=O)C.CCCCC>C1(C)C=CC=CC=1>[CH3:9][N:8]1[C:7]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=2)([CH2:6][N:1]2[CH:5]=[N:4][CH:3]=[N:2]2)[CH2:30][CH:29](/[CH:28]=[CH:27]/[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:10]1

Participants

5

Reactant 3

HCID 5371758(E)-1-Phenyl-1,3-butadieneHCID 22335286Ethyl acetate pentaneHCID 1317157282-(1H-1,2,4-triazol-1-yl)-N-methyl-1-(2-naphthalenyl)ethanimine N-oxide

Product 1

HCID 143288852-Methyl-3-(2-naphthalenyl)-5-(2-trans-phenylethenyl)-3-(1H-1,2,4-triazol-1-ylmethyl)isoxazolidine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-(1H-1,2,4-triazol-1-yl)-N-methyl-1-(2-naphthalenyl)ethanimine N-oxide (15.0 g, 0.056 mol) and trans-1-phenyl-1,3-butadiene (11.0 g, 0.084 mol) in 500 ml toluene is heated to 95°-105° C. for 48 hours, then cooled and evaporated to dryness. The resulting oil is decolorized with carbon and purified by flash chromatography on silica gel (eluent comprised of 90% ethyl acetate and 10% hexane by volume) giving two diastereomers. Isomer A (5.66 g) has a melting point of 80°-84° C. (ethyl acetate-pentane). Isomer B (1.64 g) has a melting point 157°-160° C.

Workup

  1. temperatureis heated to 95°-105° C. for 48 hours
  2. temperaturecooled
  3. customevaporated to dryness
  4. custompurified by flash chromatography on silica gel (eluent comprised of 90% ethyl acetate and 10% hexane by volume)
  5. customgiving two diastereomers

Sources & evidence

ORD record
ord-5a5830486caf4ebb96af60b3b8f50333
Source dataset
uspto-grants-1988_10
Patent number
US04777263

Reaction notes

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