Dichloromethane → 6-Chloromethyl-3-[3-[4-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethyl-phenoxy]-propyl]-pyridine

HRID 53224Notes

Reaction equation

HRID 53224 reaction equation
[CH3:1][C:2]1[N+:7]([O-])=[CH:6][C:5]([CH2:9][CH2:10][CH2:11][O:12][C:13]2[C:18]([CH3:19])=[CH:17][C:16]([C:20]3[N:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[O:22][N:21]=3)=[CH:15][C:14]=2[CH3:29])=[CH:4][CH:3]=1.C(N(CC)CC)C.C(Cl)[Cl:38]>>[Cl:38][CH2:1][C:2]1[N:7]=[CH:6][C:5]([CH2:9][CH2:10][CH2:11][O:12][C:13]2[C:18]([CH3:19])=[CH:17][C:16]([C:20]3[N:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[O:22][N:21]=3)=[CH:15][C:14]=2[CH3:29])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6344Dichloromethane3×HCID 8471TriethylamineHCID 190820506-methyl-3-[3-[4-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]-propyl]-pyridine-N-oxide

Product 1

HCID 190820316-Chloromethyl-3-[3-[4-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethyl-phenoxy]-propyl]-pyridineYield 31%

Procedure

To a solution of 1.8 g (4.4 mmol) of 6-methyl-3-[3-[4-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethylphenoxy]-propyl]-pyridine-N-oxide in 18 ml of methylene chloride was added dropwise a solution of 0.41 ml (1.13 eq) POC13 in 4 ml of methylene chloride. After addition of 10% of POC13 solution, triethylamine (0.54 ml; 1.1 eq) in 4 ml of methylene chloride was added in portions. The exothermic mixture was stirred for 30 min, washed with saturated ammonium chloride solution, and the organic layer was separated and dried over sodium sulfate. The organic layer was concentrated in vacuo and purified by flash filtration through silica gel (hexane/ether, 2:1) to afford 0.59 g (31%) of 6-chloromethyl-3-[3-[4-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)-2,6-dimethyl-phenoxy]-propyl]-pyridine (BIL-1991-187), as a pale yellow oil which solidified upon standing, m.p. 79°-81° C.

Workup

  1. additionwas added in portions
  2. washwashed with saturated ammonium chloride solution
  3. customthe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. concentrationThe organic layer was concentrated in vacuo
  6. filtrationpurified by flash filtration through silica gel (hexane/ether, 2:1)

Sources & evidence

ORD record
ord-7a690a7e19154102a8fa9d6093e3717e
Source dataset
uspto-grants-1997_04
Patent number
US05618821

Reaction notes

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