1-Octadecene → 3-Phenyl-3-(1H-1,2,4-triazol-1-ylmethyl)-2-methyl-5-n-hexylisoxazolidine

HRID 35739

Reaction equation

HRID 35739 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[N+:15]([O-:17])[CH3:16])[CH2:9][N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)=[CH:4][CH:3]=1.[CH2:18]=[CH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]CCCCCCCCCC>>[C:5]1([C:8]2([CH2:9][N:10]3[CH:14]=[N:13][CH:12]=[N:11]3)[CH2:18][CH:19]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[O:17][N:15]2[CH3:16])[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1

Participants

3

Reactant 2

HCID 82171-OctadeceneHCID 727284561-(4-chlorophenyl)-N-methyl-2-(1H-1,2,4-triazol-1-yl)ethanimine N-oxide

Product 1

HCID 143264423-Phenyl-3-(1H-1,2,4-triazol-1-ylmethyl)-2-methyl-5-n-hexylisoxazolidine

Procedure

Derivative 3 (R=H, n=5) is prepared by a procedure similar to that described in Example 1 by reacting 1-phenyl-N-methyl-2-(1H-1,2,4-triazol-1-yl)ethanimine N-oxide (1: R=H) with 1-octene (2: n=5). The resulting cis- and trans-diastereomeric mixture of compound 3 (R=H, n=5) is flash-chromatographed on neutral silica gel using as eluent a 98:2 by volume mixture of chloroform-methanol. Isomer A has a melting point of 93°-99° C. (ethyl acetate).

Workup

  1. customDerivative 3 (R=H, n=5) is prepared by a procedure similar to
  2. customis flash-chromatographed on neutral silica gel using as eluent a 98:2
  3. additionby volume mixture of chloroform-methanol

Sources & evidence

ORD record
ord-c0211e96340a4d94b767e66a51de33dc
Source dataset
uspto-grants-1988_08
Patent number
US04767866

Linked notes

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