Allyl 4-chlorobenzyl ether → 5-{[(4-Chlorophenyl)methoxy]methyl}-3-(4-chlorophenyl)-3-(1H-imidazol-1-ylmethyl)-2-methylisoxazolidine

HRID 35741Notes

Reaction equation

HRID 35741 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[N+:15]([O-:17])[CH3:16])[CH2:9][N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)=[CH:4][CH:3]=1.[Cl:18][C:19]1[CH:29]=[CH:28][C:22]([CH2:23][O:24][CH2:25][CH:26]=[CH2:27])=[CH:21][CH:20]=1>>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([CH2:23][O:24][CH2:25][CH:26]2[O:17][N:15]([CH3:16])[C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)([CH2:9][N:10]3[CH:14]=[CH:13][N:12]=[CH:11]3)[CH2:27]2)=[CH:28][CH:29]=1

Participants

3

Reactant 2

HCID 15089967Allyl 4-chlorobenzyl etherHCID 727271741-(4-chlorophenyl)-2-(1H-imidazol-1-yl)-N-methylethanimine N-oxide

Product 1

HCID 143264515-{[(4-Chlorophenyl)methoxy]methyl}-3-(4-chlorophenyl)-3-(1H-imidazol-1-ylmethyl)-2-methylisoxazolidine

Procedure

Derivative 3 (R1 =4-Cl, R2 =CH2C6H4Cl-4 is prepared by a procedure similar to that described in Example 1 by reacting 1-(4-chlorophenyl)-2-(1H-imidazol-1-yl)-N-methylethanimine N-oxide (1: R1 =4-Cl) with allyl 4-chlorobenzyl ether (2: R2 =CH2C6H4Cl-4). The resulting cis-/trans-diastereomeric mixture of the title compound (3: R1 =4-Cl, R2 =CH2C6H4Cl-4) is flash-chromatographed on neutral silica gel using chloroform-methanol (98:2 by volume) as eluent.

Sources & evidence

ORD record
ord-7c3ca5ff5259472ca908db97401407ef
Source dataset
uspto-grants-1988_08
Patent number
US04767867

Reaction notes

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